


Experimentation

by butterflybeautyrush



Category: Supernatural
Genre: Accidentally On Purpose Voyeurism, Anal Fingering, Anal Sex, Awkward Dean, Blushing Dean, Bottom Dean, Cock Slut Dean, Dean in Panties, Dirty Talk, First Time, Improvised Sex Toys, M/M, Masturbation, Mild Praise Kink, Minor Non-con situation, Object Insertion, One Night Stands, Panty Kink, Pegging, Praise, Pre-Series, Rimming, Self-Doubt, Strap-Ons, Underage - Freeform, Vibrators, Vulnerable Dean, almost het sex, het interactions, inexperienced dean, mild kink negotiation
Language: English
Status: In-Progress
Published: 2016-01-18
Updated: 2018-04-15
Packaged: 2018-05-14 16:23:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 10
Words: 34,717
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5750017
Author URL: https://archiveofourown.org/users/butterflybeautyrush/pseuds/butterflybeautyrush
Summary: <blockquote class="userstuff">
              <p>At 18, Dean is beginning to realize he may not be as straight as he thought.  Home alone, he is finally able to experiment and well...he just can't seem to stop.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This story is cross-posted on ff.net and Sinful Desire under the same pen-name.
> 
> Disclaimer: Supernatural and its characters do not belong to me. The smut however is mine ;)
> 
> My second Supernatural story to date, though this one contains far less substance. Onto the pwp!

With Sammy out at school for the day and Dad out on a hunt, Dean was at their latest home alone. A call from his boss at the car shop told Dean he had the day off and now Dean was feeling a little antsy – nothing better to do than sit on his ass and watch TV. After aimlessly flicking through channels all morning, Dean sighed and launched the remote across the room. He was bored and feeling useless…and bored. He popped his lips a few times, drumming his fingers on his knees. There had to be something he could do.

 

After another few minutes of aimlessly lying around, Dean sat up straight on the lumpy old couch, a smile slowly spreading across his face even as his cheeks flushed a light red in response to his thoughts. With only a second of hesitation Dean went into the back of the house where he and Sammy shared a room and bent to retrieve his duffle bag from underneath his bed. Rifling through his clothes, Dean pulled out his hair gel, an old hairbrush he hadn’t used in forever and incidentally forgotten about, a spare knife, and finally what he was looking for, an old issue of Busty Asian Beauties, a place he knew his brother would never intrude on. Opening it to the centerfold, Dean slid out what he’d really wanted – the risqué, distinctly male-centered, obviously gay, magazine he’d smuggled into his bag over three weeks ago. Until now, he hadn’t had an opportunity to look at it and with a few hours yet until Sam returned home, Dean was finally getting his chance.

 

At 18 years old, Dean was only just now beginning to realize his sexual preferences weren’t exactly traditional. For years he’d been conditioned to want girls, women, whatever, to think sleeping with girls was something to be proud of and to brag about, a symbol of his virility, his strength as a man. Even now, Dean was having a hard time reconciling those beliefs with what he kind of knew was true about himself; as attractive as girls could be, they weren’t what he wanted. It seemed muscled lean bodies were more his thing. Problem was, Dean couldn’t be positive because as much as he thought the male form appealed to him, he didn’t have any experience to prove it. He’d been with girls, made a reputation for himself in being with a large number of them, even enjoyed himself, but he had no experience with guys to prove that would be better. The magazine had really been his first chance to prove it to himself, but until now he had never been alone long enough to start experimenting.

 

Standing up, Dean dropped the other magazine on his duffle, turning to sit on the edge of his bed and gingerly turning the first glossy page of the new one. He ran a hand through his hair and breathed deeply, trying not to think too hard about what he was doing. His breath hitched at the sight before him – a man, probably not too far into his twenties, leaning against a wall in only his tank, rucked up to show one dusky nipple, and his underwear, fingers cupped around the hefty bulge of his cock. The man was biting his lip, staring directly into the camera, a light sheen of sweat covering his skin. Dean couldn’t breathe. This was so much hotter than any other magazine he’d looked at before.

 

Forcing a breath through his nose, Dean rubbed his sweaty palm against the denim of his jeans. He flipped the page, finding another young man, this time somehow in an even more provocative pose. Dean found himself biting his lip, so far resisting the temptation to touch his rapidly hardening dick. Another page and he couldn’t take it anymore. Dean dropped the mag on the bed and stood, shucking his jeans and underwear as fast as possible before yanking of his socks and t-shirt off in the length of three heartbeats.

 

He settled back onto the bed, this time leaning back against his pillow and the headboard, his legs stretched out in front of him. When he picked up the magazine again, his right hand instantly gravitated to his groin, timid fingers wrapping around the base and moving in a slow slide up. After that the movements were mindless, uncontrolled; Dean couldn’t get enough. He could feel the blood pounding through his veins, the pulse of it in his cock, the tension in his thighs as the pleasure heightened.

 

On the next page were smaller pictures and some feature articles. He almost flipped right past them when a word caught his eye: prostate. Eyes flicking to the top, Dean’s hand froze mid-stroke. The article was talking about sex and adventurous ways to stimulate that sensitive gland. Shit. The other magazines he had never went into quite as much detail as that. This was starting to seem more like an instructional manual. Where the hell had this thing come from?

 

Dean skimmed the article, extremely aware of the blush covering his cheeks. He had slowly started to stroke himself again, but he couldn’t tell if he was more excited now or intimidated. Feeling his skin prickle in the cool air, Dean’s hips lifted into his hand. Excited it was.

 

Feeling emboldened, Dean shuffled the magazine to the side, sliding down on the mattress so he was lying mostly flat on his back. A few more even strokes to his cock to get his rhythm back and Dean let his legs fall open, parts he usually didn’t think about on display, exposed. Dean’s head rocked back against the pillow, strangely aroused by what he was doing. He continued stroking, switching hands so he could cup and tug his balls, and then his right hand was adventuring further down than it had ever gone before, skimming lightly over the skin, following the crack of his ass down and back up until his finger-tips were resting right over his rim.

 

He stopped. No freaking way was he doing this. He couldn’t.

 

And yet…the fingers were already pressing a little harder, exploring the texture of the wrinkled flesh, massaging the skin even as it retracted under his touch. Dean felt light-headed. He forced himself to breathe, sucking in air while his fingers remained in place. He wanted nothing more in that moment than to go further, to press inside, explore, just touch and experience, but he was nervous. He forced another few breaths and sat up, pulling both hands off of his body. If he was going to do this, he would need something to ease the way. Even with no experience in this area, Dean knew enough to know some sort of lubrication was necessary.

 

Dean leaned over the side of the bed. He saw the bottle of hair gel, almost reached for it and cringed. That stuff was way too sticky to make things even remotely comfortable. Going into the bathroom, Dean returned with a bottle of lotion and some tissues. Biting his lip, Dean once more situated himself on the bed and leaned back, this time with lotion in hand. He eased himself back into it, stroking his cock, rubbing his balls, and then finally returned a finger to his crease, ghosting over the sensitive skin. His lungs froze in action once more.

 

Pulling his hands away, Dean reached for the lotion, globbing some onto his fingers and then reached back between his legs to smear it over his rim. He hissed at how cold it felt, but gradually relaxed as the cream warmed on his skin. For a few long minutes, he couldn’t bring himself to do anything more than massage the skin around his hole, but as he grew more comfortable, Dean dared to press a little bit harder. He held his breath and pressed down with one finger, sinking in only to the end of his nail before stopping. Panting breaths escaped his throat. He didn’t know if he could do this. Pulling back out, he gathered some of the excess lotion on his skin and pressed against his hole for the second time. This time he made it to the first knuckle before freezing.

 

If he did this he would never be able to go back. Dean knew that. He knew, even more than he knew that monsters existed, that if he continued on this path, that he would never be able to go back to women, to being what his father wanted. For a moment, Dean considered pulling out, had even started moving his finger, but before he could consciously make the decision, his finger was pressing deeper, surging within his body and sealing his fate.

 

With a finger fully embedded in his ass, Dean moaned and rocked his hips, turning his face into the pillow to avoid making a louder sound. His heart was racing, a loud thumping beat that felt as if it could escape right out of his chest. Pulling the finger nearly out, Dean wiggled it just inside the rim and whimpered, gasping as he plunged it back inside. This time he didn't stop, simply pulled back and did it again, and again, until he had a built a rhythm.

 

Minutes later, Dean wanted more and so he retracted his fingers and added more lotion, returning with two. He pressed gently, nervous about introducing more width to his tight hole. Rather than the fierce resistance he expected however, Dean was met with a welcoming suction, the two fingers swallowed as deeply as possible in a matter of seconds. A loud moan filled the room. Wiggling the fingers around, Dean tried separating them, pleased when he was able to and then he cut off a scream as a bolt of pleasure shot up his spine. Fuck. That had to be what the magazine was talking about. He’d found his prostate.

 

Slowly, experimentally, Dean spread his fingers again, and when the same feeling didn’t spread through his body, he pushed his fingers back together and plunged them at an angle into his body. After a few erratic thrusts inside, Dean’s back arched off the bed as a primal cry left his lips. He’d found it. For a few seconds Dean kept his fingers in place, dragging them repeatedly over the sensitive area, a scream finally breaking free when the sensation became too much. His body shook and went still, his fingers still buried inside.

 

Pulling out for more lotion, Dean panted. He wanted more. In seconds, he had replaced two fingers with three and was again thrusting inside his body with a bit too much force. Colliding with the nerves again, Dean sobbed and then did it again before leaving the spot alone long enough to try spreading his fingers. Now with three fingers, Dean found stretching his hole was much easier, the muscles relaxing incrementally with each thrust inside.

 

Every thrust heightened the pleasure spreading through Dean’s veins. He’d never felt anything like this before and wanted nothing more than for the sensations to never stop. Legs splayed wide, Dean lifted his hips, keeping the rhythm. Only when he felt the heat pool in his belly did Dean wrap his left hand around his cock, adding to the pleasure surging through his body and finally pushing him over the edge.

 

White stripes painted his belly as his back arched away from the mattress, his hole pulsing around his fingers. Flicking the digits one last time over his prostate, Dean whimpered and collapsed back against the bed, body drained of energy. After a few breaths, he pulled his fingers from his hole and sighed at the emptiness, reaching for the tissues and cleaning up his belly.

 

Sitting up, Dean groaned at the twinge in his ass. Shit, even after all that he wanted more.

**Notes for the Chapter:**

> This is the first in a series of chapters. The exact amount is yet to be determined. I currently have the second chapter written, the third planned, and ideas for more after that, but we'll see what happens.
> 
> Let me know what you think! Feedback will actually get those next chapters posted.
> 
> Hope you enjoyed!
> 
> Side Note: This story will potentially be Dean/Sam slash, but I haven't decided yet if I want to venture into relationship territory or just leave it with Dean. Opinions would be greatly appreciated :)


	2. Chapter 2

**Notes for the Chapter:**

> And chapter 2 is here as promised! Enjoy!
> 
> Warning: Use of unconventional sex toys ahead

Going into the bathroom, Dean wiped his stomach down with a wet cloth, sighing with relief now that he felt clean. He dropped the cloth to the floor and stared at himself in the mirror. His hair was in disarray, cheeks and chest flushed red, pupils blown, and bottom lip swollen from constant biting. Dean closed his eyes against the image and bent to splash water over his face. He was so screwed.

 

Back in the bedroom, Dean caught sight of the magazine and flushed, looking at the floor. If his dad ever found out…oh god, he was so fucked. Avoiding the problem and seeing the mess of stuff he’d left out, he knelt to put it all away, tossing the clothes, gel, and knife back into the bag before freezing when he got to the brush. His eyes darted between it and the magazine on the bed, flicking back and forth as his brain raced. Could he?

 

No. Fuck no. But…shit.

 

Dean stood with the brush in hand, duffle left forgotten on the floor as he climbed back onto the mattress. Situated on the bed once more, Dean stared at the object in his hands, a brush with a round handle, not very big around, a domed tip – perfect for what he had in mind. Oh fuck, he was doing this.

 

Leaning back so only his head and shoulders were lifted, Dean took a deep breath. He opened his legs and slid his hand down, fingers immediately finding the tender skin of his rim and the lotion left behind from his last foray only ten minutes before. Swallowing thickly, Dean pressed two fingers back into his hole, breath hitching when they slid right in. He gave a few experimental thrusts before pulling back out, Dean’s dick twitching where it lay against his thigh.

 

Fuck. “Might be gay” was in the dust.

 

Patting the bed, Dean located the tube of lotion and grabbing the brush, applied a thick line of it down each side of the handle. If he was doing this, he was making it as easy as possible. With a deep breath Dean dropped the tube back to the bed and using his right hand, situated the brush handle so the tip rested against his hole. Cock starting to perk up, Dean lifted his head to watch, fascinated as he just barely pressed the tip inside.

 

This experience was much different than his fingers. Where his fingers were warm and pliable, the brush handle was rigid, unforgiving, and cool to the touch. He blinked against the sweat dripping down his forehead. He wanted this. He could do this.

 

Inhaling deeply, Dean pushed the shaft slowly inside himself, releasing his breath with each nudge inside. Gripping the bristled end now, Dean stopped halfway, panting. He closed his eyes and then opening them to watch once more, pushed with a steady pressure until the entire length of the shaft was buried inside him.

 

Dean’s head rocked back as a loud whimper rose past his lips. The handle felt huge inside him, pressing further than his fingers had reached, holding him open in a way his fingers hadn’t. While it wasn’t as wide as the fingers, Dean felt like this was more what a real cock would be like, hard and long, reaching so deep inside him. He moaned.

 

With another whimper, Dean rocked down onto the handle, using both hands now to push it in and out of his body at an even pace. As his muscles became more accustomed to the movement, he increased the speed, finally just keeping his hips raised off the mattress and plowing himself wildly with the toy. Fuck, this was amazing.

 

The lotion allowed the handle to slip in and out without dragging and trying something a little different, Dean pressed the brush handle in as far as it would go…and pulled the bristled end up towards his balls so the handle angled down, then pressed the top down into the mattress so the handle angled upward. Dean’s whole body writhed at the new sensation and after cycling quickly through those motions at least a dozen times and hitting his prostate a fair amount, Dean was feeling so oversensitive and close to coming he had to stop.

 

Holding himself still for a few beats, Dean breathed deeply and then tried something else, something that would hopefully feel just as good without being so overwhelming. This time he pressed the handle in to its base and then twisted, the shaft rotating inside him and pulling against, almost tickling, his walls as it turned. A burst of laughter left him, followed quickly by a moan.

 

As much as Dean was enjoying all this, the experience was still new and he could feel his body reaching its limit. He would come soon and there was little he could do to stop it.

 

Dean stopped twisting and returned to a regular thrusting motion, trying different angles as he filled himself over and over again with the unconventional toy. Wanting to try one last thing before he came, Dean pulled the handle free from his body and turned so he rested on his hands and knees, dropping down so his cheek pressed into the pillow, ass in the air.

 

A bright blush flooded his cheeks again, but Dean ignored it in favor of returning the toy to his hole. Keeping his legs spread, he reached under his body with both hands and nudged the tip inside, before sliding it home, his hips rocking back desperately as the base met his cheeks. The new angle forced a sob out of his throat.

 

After one experimental thrust in and out, Dean renewed the frenzy of before, spearing his hole with the shaft over and over and over again as whimpering moans surged from deep in his chest. A low burning heat was building in his blood, filling his belly and tightening his balls.

 

With one more hit to his prostate and two last deep thrusts, Dean’s body went rigid as he reached his peak. Completely untouched, his cock spilled white streams onto the sheets below him, hips rocking back against the shaft, hole clenching tightly around it. Dean bit his lip against the scream that wanted to fill the air, turning his face into the pillows when the surges of pleasure became too much.

 

As the aftershocks faded, Dean collapsed, body falling flat, the handle still lodged inside him. He panted, eyes closed, waiting for strength to come back into his limbs. He’d never felt so drained after an orgasm before. Fuck, he had to do that again soon.

 

Feeling returning to his fingers and toes, Dean dragged his arms out from under his body and reached behind him, slowly pulling the brush handle from his hole. He gasped as it popped free, ass clenching around empty air.

 

Dropping the brush on the bed beside him, Dean squirmed, the cooling wet spot under his belly growing increasingly uncomfortable. With a groan, he heaved himself up and stumbled to the bathroom to wipe himself down for the second time that day.

 

***

 

That evening after picking Sam up from school, Dean went out to the Impala to gather up a duffle bag worth of weapons to clean and prepare for future hunts. Even though everything was always cleaned after a hunt, they could never be too careful, and well, Dean was bored. The smell of gun-oil and the rhythmic snicking sound of blade on whetstone was soothing and Dean’s nerves were thrumming after the day he’d had.

 

Rooting around in the trunk, Dean piled another blade onto the heap filling his bag. Reaching a little further back, and shifting a shotgun out of the way, Dean’s breath hitched, his fingers coming into contact with the biting cold metal of an old MagLite flashlight.

 

Curling his fingers around the cylinder, Dean dragged his hand back, a huff of breath breaching his lips once all fourteen inches rested in his palm. Shit, the weight of the flashlight was holding him in place, almost like it possessed its own gravitational pull.

 

Dean stared, mouth dry, swallowing thickly as he imagined everything he could do with the object in his hand. A little larger around than his three fingers combined, it would stretch him so perfectly, and big even without counting the flared top, it was long enough that he wouldn’t have to stop at any particular depth like with the brush.

 

Just picturing himself mounted on the shaft made his dick twitch in his pants, palms suddenly sticky with sweat. He rubbed his left hand dry on his jeans, shooting glances at the door to the house. He was all too aware of Sam’s presence in the house and as much as he wanted, god he wanted, to put the vivid images into action, he knew he had to wait.

 

Forcing a deep breath, Dean tucked the flashlight into the duffle and stepped back, slamming the trunk closed and loping into the house. He couldn’t wait for his next day off.

 

**Notes for the Chapter:**

> I so enjoy a young, semi-innocent Dean.... Next part should follow soon :)


	3. Chapter 3

**Notes for the Chapter:**

> Thanks so much to everyone who has followed/favorited this story so far! It’s kept me writing. I’m so sorry for the long wait! After lots of long workdays and the start of a new semester I finally managed to get this part finished, so here it is! Enjoy!

As is the case whenever he wanted something however, Dean’s next day off didn’t come for another week and a half. He had to make due with jerking off in the shower, maybe slipping a few fingers into his eager hole if he had enough time, until finally he was let out of work early the following Thursday. After servicing only one car, he’d been told there were no other appointments scheduled for the day and if anyone came in, the other men still working could handle it.

 

Luckily, their dad wasn’t due home for another couple days, later than planned after finding another case a state over from the last one, and it was the middle of the week so Sam was still in school. Dean brushed his grease-slicked hands against his thighs, whistling as he tossed down his rag and retrieved his jacket, loping back out to his car for the fastest ride home since starting his job at Hal’s, the local mechanics.

 

Back in the room he shared with Sam, Dean dropped to his knees and dug his duffle bag out from under the bed, fumbling through his clothes and other belongings until he unearthed the MagLite he’d stashed there over a week ago. He forced an even breath through his lips.

 

Holding the flashlight and knowing that now was the time he’d actually use it, Dean was feeling a bit intimidated. It was huge after all, bigger and longer than his fingers or the brush handle, and as much as he’d been using his fingers recently, there was no way those minimal forays could compete or in any way really prepare him to take the thick width of the metal shaft. Dean’s breathing sped up, his heart starting to race. He didn’t know if he could do this. It had sounded good at the time, coming off of his orgasmic high, but now, completely in his right mind, the prospect of putting the thing inside him seemed increasingly more daunting.

 

And yet there was nothing Dean had wanted more in the past week than to take something bigger, feel fuller than his fingers managed to make him feel. He’d tried the brush again once or twice when he could sneak it into the shower with him, but the chance of getting caught was too great with his brother in the house. Fingers were safer, at least for the time being, and they were what Dean had to settle for until he had time to himself.

 

Now that that time was here, Dean hesitated to pass up the opportunity. Bracing his hand against the mattress, Dean pushed himself to his feet, dropping the flashlight onto the bed. Swallowing thickly and taking a deep cleansing breath, Dean undid the button on his jeans and lowered the zipper, tucking his thumbs under his waistband and shoving them down along with his boxers before he could change his mind.

 

Having kicked off his pants and discarded his flannel and t-shirt, Dean sank down onto the bed and took the flashlight in hand, running a hand through his hair as he stared at the size of it. Curling his fingers, his thumb and middle finger were thankfully able to meet around its edge, but just barely, and Dean swallowed at the sheer idea of that size anything fitting inside him. Then again, if he ever wanted to have actual sex with a man, this would be good practice. If he couldn’t take this, there was little chance he’d ever make it to having a real cock inside him…and he wanted that – wanted it bad.

 

With as much conviction as possible, Dean leaned back on the bed, letting the flashlight fall to the sheets. He swept his right hand down over his stomach, ghosting over the flesh and leaving goose bumps in his wake, before sweeping back up over his chest and stopping to tweak a nipple. His back arched, a satisfied moan leaving his lips. This was familiar territory.

 

After a few minutes of teasing himself, heightening his sensitivity, Dean finally took hold of his dick, starting with slow long pulls and then after smearing pre-come up and down his length, started jerking his wrist faster with little twists at the head. Bursts of pleasure flooded his system and Dean was instantly more comfortable, his body more fluid, movements less hesitant.

 

Growing bolder, Dean raised his other hand and teased at his balls, lowering his right to brush over his crease. His breath caught in his throat, teeth coming down to dent his bottom lip. Dean spread his legs wide across the mattress and bent his knees, using two fingers to massage the skin around his hole. His fingers nudged at the wrinkled skin, using gentle pressure to tease himself while his left hand kept up a slow loose rhythm over his cock.

 

The lingering tease was making Dean’s blood sing, anticipation making the hair on his arms stand up. Needing more, Dean reached over the side of the bed and felt around for the bottle of lotion. He popped the cap and slicked his fingers, tossing the bottle down as he returned his fingers to his hole. Now lubricated, the first finger slid inside with little effort, Dean’s ass accepting the intrusion gratefully. Less than a minute later Dean added a second finger, and then a third, gasping out near silent moans as he increased the depth and speed of his thrusts.

 

With hips rocking down onto his fingers and up into his fist, Dean’s body was thrumming with pleasure and so eager for more he could barely stand it. Another push inside and Dean forced himself to pull out, hole clenching in earnest as he rolled to his knees.

 

Sitting back on his heels, Dean braced his hands on his thighs, taking a few deep breaths before grabbing the flashlight. If he thought about it too much he might back out and honestly, that was the last thing Dean wanted.

 

Dean draped himself over the side of the bed one last time, this time retrieving a condom from his bag. Even though he’d sanitized the length of the flashlight, twice, Dean didn’t want to take any chances on whatever had gathered in the back of the trunk. Hopefully the thin latex sheath would help smooth the flashlight’s entry into his body too.

 

One more time Dean smeared a finger full of lotion over his hole, pressing just past his rim to make the entry as easy as possible. His fingers shook as they left his skin, nerves surfacing in the midst of Dean’s excitement. A little more lotion went onto the length of the flashlight, as much as Dean could manage without his hands slipping off.

 

Balanced on the bed, Dean lifted up on his knees, situating the flashlight, bulb down, between his legs, about even with his ass. Shit, he was so fucking nervous. Holding his breath and hands firmly gripping the flared base of the MagLite, Dean pushed down, flinching when his heated skin met the cold metal. He used one hand to guide the tip to his hole and pressing down, managed to wedge the very top inside, hissing at the uncomfortable pressure of being spread so wide.

 

Dean concentrated on breathing, his lungs stinging as he forcibly inhaled. Fuck, it was huge – so big inside him. He closed his eyes and lowered himself down, biting his lip and tipping his head back at the discomfort. This was nothing like the brush handle, so much bigger it was verging on unmanageable.

 

Sucking in another breath, Dean rocked on the metal shaft, groaning as the motion seemed to spread him wider. Another rock and Dean felt the length slide an inch deeper, and unable to take any more for the moment, Dean lifted back up and slowly dropped down, biting his lip as he took a little more than the last time. His lungs were fighting for air, eyes tearing as his hole swallowed the thick shaft.

 

Hands braced at the base, Dean circled his hips, head falling back as an icy hot shiver wracked his spine. A sobbed moan broke from his throat, his hips jerking hard against the sensation. There it was. Fuck, again. He needed it again.

 

Dean’s hips moved uncontrollably, a frenzied circling and rocking, trying to stay as far down on the shaft as he could manage and keep up the pleasurable sensation. Every time the rubber-coated shaft dragged against his prostate, a soft moan filtered through the room. Dean couldn’t control it and he loved it. It felt fucking amazing.

 

Thigh muscles clenched tightly, Dean kept rocking, gradually working up to a bounce, pulling almost off the shaft before dropping back down, cock slapping against his belly with each movement. Heat spread through his body, made his extremities tingle and sweat bead on his skin. He rode the flashlight’s length as fast as he could, stopping every few thrusts to grind his hips, gasping every time the shaft scraped past the sensitive gland. His eyes were rolling in his head and Dean bit his lip to stifle a moan.

 

He knew he was getting close, the heat racing up his back, flushing his chest and his cheeks, his balls growing heavier by the second. It wouldn’t be much longer now and Dean slammed himself down on the long shaft, a whimpered cry blurting past his lips as the shaft sank deeper inside him. Oh fuck, too much, too full, but oh so good. Dean licked his lips, short mumbled moans bursting out on every bounce now, his thighs trembling so much Dean’s almost fell face first into the mattress.

 

He rebalanced and moved one hand to his cock, pumping in a hurried motion to push himself over the edge. His thrusts became erratic, hips unable to keep an even pace, and just as the flashlight shaft rubbed hard once more over his prostate, Dean’s head rocked back, a gasped moan signaling his orgasm.

 

Heat. God, white heat, can’t see, oh fuck so good. Dean’s whole body went rigid, the flashlight buried deep inside him, his hips still rocking as aftershocks shook him. His hand worked his cock through the climax, wringing out every drop of his release. It coated his fingers and his belly, some even dripping down onto his thighs and the comforter on his bed. Absently, he knew he’d have to clean that up, but right now he was floating. Honest to god floating, blurry vision and everything.

 

Still panting, Dean pulled his hand away from his dick, reaching for the tissues on the nightstand and wincing when the flashlight was jolted against his sensitive insides. After he cleaned up the mess he gingerly lifted up, breathing deeply as the length slipped free of his hole. Dean let the metal shaft fall to the bedspread, fingers going back to his hole to probe at the tender skin.

 

Hearing the squeak of a floorboard, Dean’s head jerked towards the doorway, a startled yelp escaping his throat as he fumbled his blankets over his lap. His cheeks flushed beet red and Dean wanted to sink through the floor. He was tempted to throw the flashlight as far away from him as possible, the lotion bottle too, but stopped himself knowing it would only draw more attention to what he’d been doing.

 

Fucking Sam. His 14 year old little brother was standing in the doorway and Dean had never felt more trapped, not even on a hunt with evil staring him down. Shit, shit, shit. Dean was fucked. Oh god was he ever – in more ways than one. He almost burst into hysterical laughter as his thoughts reflected on his activities only minutes ago. Shit.

 

Panicked and incredibly uncomfortable, Dean tried to pull the blankets higher on his body, tongue immobile in his mouth. He just stared at Sam, every second bringing him closer to tears…or shouting – Dean couldn’t be sure.

 

“Hey De’,” Sam greeted sheepishly, head tilted down in a modicum of embarrassment. Dean just stared with wide eyes, hands shaking where they were curled into the bedclothes. “Had a half day. Sorry bro, thought you knew.”

 

Dean’s jaw was clenched, and his eyebrows rose at Sam’s comment. Half day – a fucking half day.

 

“Sorry I interrupted. I uh – didn't mean to make any noise. You looked like you were really enjoying yourself.” Sam’s cheeks flamed bright, but his eyes were eager and as Dean looked closer, slightly dilated.

 

Shit, “How long were you there?” Dean croaked, his throat incredibly dry.

 

Sam ducked his head and bit his lip telling Dean what he needed to know. His brother had walked in on him and stayed to watch. Dean nodded sharply, a short bob of his head. He didn’t know what to make of that. Sammy, his little brother, but also Sammy, a teenager bound to be interested in sex.

 

“Maybe next time you should uh go to the internet for the free porn.” It was half nervous joking and half serious. Is that what it had been for Sam? A chance moment to get his rocks off…or was it just that he’d walked in and been unable to stop – like a car crash you couldn’t help but watch unfold.

 

Sam’s brows drew together, his lips pursing in a frown. “Come on Dean, that’s not what this was.” His hands were balled into fists at his sides, and yet there was also a bulge in his pants, seemingly getting smaller but still there.

 

“Oh no?” Dean challenged gruffly, lifting one brow and gesturing at his brother’s groin with his chin. He felt mean, vindictive even, and Dean wasn’t usually like that with Sammy. He didn’t like it. But he also didn’t like feeling cornered and he didn’t know how to deal with his current situation, so as usual he lashed out.

 

“Don’t be a dick Dean,” Sam bit out, turning away. “You should just take it as a compliment,” he threw over his shoulder as he stomped back out into the hallway.

 

Dean drew back as if hit and stared after his brother. His whole body was shaking now, with adrenaline or anger or fear he wasn’t sure. What he did know was that Sam had grown up a lot more than he’d permitted himself to see recently. He was growing up, getting bolder, and Dean didn’t know how to handle that, because instead of little Sammy who’d he’d cared for all his life, there was almost adult Sammy who was growing taller and more muscular and who had managed to get under his skin in a way he never expected.  


Dean felt his dick twitch where it rested against his thigh under the blankets and dropped his chin against his chest with a groan. Seeing his brother worked up, turned on, because of him was somehow exhilarating and arousing, and completely inappropriate. And Dean couldn’t help himself. Thinking back, he pictured Sam in the doorway as he rocked on the flashlight shaft, imagined how Sam’s eyes would have dilated as he watched, how he might have bit his lip to keep himself quiet, how he maybe palmed himself just to provide the barest hint of pressure.

 

Dean groaned and flopped back onto his bed in frustration, closing his eyes against the image of his now fully erect cock lifting the blankets off his skin. He banged his head back on the mattress and lifted a tentative hand to his dick. Yeah, yeah he was doing this.

 

**Notes for the Chapter:**

> I hope this chapter made up for the long wait :) I decided to go for the Sam/Dean dynamic after all, so I'll just have to see where it takes me! Comment and let me know what you think!


	4. Chapter 4

**Notes for the Chapter:**

> Sam becomes a little more prominent in this chapter, but they both still have a lot to learn. Enjoy :)

 

“So are you gay?” Sam asked, crunching into an apple as he flopped down on the couch next to Dean. Dean choked on the mouthful of soda he’d just sipped, nearly spraying it across his lap and the carpet in the living room. He coughed and leaned over his lap trying to breathe, throat burning, flinching when Sam rested a hand on his shoulder.

 

He sat up straight and leaned away from Sam, keeping his gaze straight ahead. “You can’t just ask people that!” he wheezed, hand cupping the base of his throat.

 

“But you’re not people, Dean. Come on, you’re my brother, you can talk to me.” There was a slight whine underlying Sam’s voice.

 

Dean stood jerkily and walked out of the room, rubbing the back of his neck, cheeks red. That was the first time Sam had brought up their voyeuristic – Dean didn’t even know _what_ to call it – from a week ago. Dad had come back from his hunting trip making most conversation impossible and Dean had been grateful. He should have expected Sam to jump at the chance to question him as soon as Dad left again and now he had to awkwardly fend off his brother’s attempts at conversation.

 

He did not want to talk about this – ever, as in he’d cut out his tongue or something equally painful before he had this discussion with his brother. Problem was, Sammy was relentless and Dean knew he had little chance of escaping his brother’s questions.

 

“So are you?” came the muffled shout from the living room. Dean groaned into his palm.

 

***

 

Over the course of the next week, Dean started noticing Sam lingering near him in ways he never had before. Sitting on the couch, Sam sat barely inches away. Cooking in the kitchen and Sam was leaning against the counter next to the stove. If Dean went into their bedroom, Sammy followed not a few minutes later, a cheery excuse on his lips for why he had to be there too.

 

Dean was getting sick of it, Sam’s constant presence driving him nuts. He couldn’t find a spare moment for himself without Sam being at school and the pressure of Sam’s eyes on him was making Dean paranoid and simultaneously turned on.

 

With Sam bent over his homework at the small table in the kitchen, Dean popped up from the couch and popped his soda can into the recycle bin. He watched Sam’s jaw clench as he flipped his pencil eraser side down on the page, rubber shavings already covering the table. Seeing his brother engrossed, Dean decided now was the perfect time to get a little distance. “I’m gonna go up and take a nap Sam,” he shared, his little brother’s head nodding absently, a breath huffing through his nose in annoyance.

 

“Right. Good luck with that.” With a knock of his fist on the counter, Dean left the kitchen and went upstairs, closing the door softly behind him. He listened through the door to make sure Sam stayed downstairs and then dropped onto his bed, a spring popping loudly under him.

 

Wriggling out of his jeans and his t-shirt, Dean hastily dropped them to the floor, stacking his pillows behind him so they gave him something to lean against. Settling back with his legs spread, Dean brushed his hand over his chest and pinched a nipple, biting his bottom lip as a spark of pleasure radiated out from the point of contact.

 

He lingered for a few minutes, tweaking his nipples, hips starting to rock into the open air above him. Not even a hand on his dick and it was ready to go, pre-come beading at the head and smacking against his belly. Turning his face into his pillow, Dean cupped his balls, rolling them in his palms before skating his fingertips up his shaft, gusts of breath hissing through his teeth.

 

It had been awhile now, the last time he’d really managed some personal time the afternoon Sam had caught him in the act. Dean wrapped his fist around himself, pulling in long quick strokes. His hips rolled up into his hand seemingly without his control. So good, god he couldn’t get enough. He needed more.

 

Just knowing he needed more, Dean switched hands, bringing his right hand to his mouth and sucking in three fingers. He closed his eyes, slightly embarrassed by what he must look like. As much as he’d adapted his thinking and accepted that the male body was more his thing, acting out his desires on his own body still kind of made him uncomfortable.

 

Trying to ignore it, Dean pulled his fingers from his lips leaving them spit-slick and swollen, and directed them down past his balls. Sucking in a breath and feeling a surge of heat light his body, Dean passed one finger over the furled muscle. A few swirls and gentle questing presses and the first one was inside, sliding right to the base. Dean moaned. It was even better than the first time, his body expecting the sensation this time around.

 

Little whimpers skipped past Dean’s lips as he added the second and third fingers, a flush flooding his cheeks as the sounds filtered into the quiet room. Still jacking his cock, Dean pushed all three fingers in as deep as he could, back arching as they grazed his sensitive walls. With a twist and a jab, Dean found his prostate. He hips jerked hard against his fingers, the hand on his cock slowing as he focused his attention on massaging the magic spot inside him.

 

For a few long minutes, Dean pounded his fingers inside himself, his throat closing around the whimpers and yes, please, oh god yeses that wanted to escape. Mid-motion, hips rolling up off the mattress, Dean froze, a loud scuffle and bump alerting him that he wasn’t alone anymore. Eyes shooting open, green met hazel as the door swung open.

 

For a long moment the brothers just stared at each other, eyes locked, bodies frozen. A stifling tension clouded the room, leaving a weight on Dean’s chest that made it hard to breath. He panted, still frozen, waiting. He couldn’t speak – and it seemed neither could Sam. They may have stared at each other for minutes before Sam’s eyes flickered away, coasting along Dean’s body and taking in his position.

 

Dean heard the soft catch that impeded Sam’s breathing and then watched as his eyes hooded, tongue darting out to wet his lips. He could feel blood rush to every surface of his body, painting him in an embarrassing pink blush, and couldn’t seem to control his hand as his fingers pushed forward, deeper inside his body.

 

From his position at the door, Sam watched raptly, swallowing heavily as Dean’s hips rocked into the movement. Dean saw his brother’s dick twitch in his jeans and couldn’t help how pleased he felt at the sight. Fingers surging forward again, they dragged over his prostate and with eyes on his brother, Dean groaned and threw his head back. Sam sagged against the doorframe, hand lifting to his groin to palm slowly at his growing erection. He couldn’t seem to help himself.

 

Strangely motivated now by Sam’s presence, Dean increased the pace, hand flying over his cock, the twisting motion at the head leaving him breathless. The fingers inside him moved a bit slower but still plunged deep and hard, a similar twisting motion drawing a gasp from his lips and causing a shudder to shake his body. His eyes slammed shut from the pure force of pleasure overtaking his body, but he willed them back open simply to be able to see Sammy standing in the doorway.

 

Dean kept up the swift motions of his hands, writhing down onto his fingers to try and get them deeper, hit his prostate harder. Stifled whimpers were crawling over his lips and Dean couldn’t even be embarrassed, so focused was he on getting himself to come. Just. Need. To. Come. The words pulsed in his head, over and over in time with his fist, eyes watering with growing desperation. “Can’t. Oh god, I can’t –” he choked, features twisting in desperation.

 

Every roll of his hips brought another wave of pleasure, sparks flying up his spine and leaving goose bumps to dust his skin. It just wasn’t enough. Dean considered finding the hairbrush in his duffle, the one he’d used a few weeks ago and stashed under his clothes, but couldn’t bring himself to stop.

 

Sam’s hand had stopped moving at his crotch, just resting over the hard bulge as he watched Dean in concern. His brows knit together and just when Dean thought he’d say something, his brother turned and ran out of the room. Dean bit his lip to stifle a whimper, eyes unmoving from the open doorway.

 

From the hallway Dean could hear the squeak of the closet door and some muffled rustling before the slam of the door echoed and Sam was running back into the room, cheeks tinged pink. He stopped a few feet from the bed, hand behind his back, head ducked, seemingly timid after his brazen staring not even minutes before. The hand on his dick slid erratically up and down, the motion verging on painful as the lotion he’d grabbed when he started began drying into his skin. The fingers still plunging frantically into his hole had started cramping and Dean groaned, unable to get himself off.

 

Lifting his head, Sam took a deep breath and strode forward, depositing himself onto the side of the bed. The mattress dipped and Dean’s hips rolled, a small cry leaving Dean’s mouth as both hands lost their rhythm. “Sorry,” Sam whispered, flicking his bangs out of his face. Flashing a shy grin, Sam looked up at Dean and removed the hand from behind his back, brandishing an electric toothbrush.

 

Dean’s hands froze in place, brows raising in confusion. He didn’t understand, just needed to get off. God, needed to come, so bad, so bad. What the hell was Sam trying to pull?

 

“Vibration’s supposed to be good, right?” He looked at Dean with big eyes, hopeful eyes. Dean nodded jerkily, still not understanding. “Well, I bought this for my teeth awhile back and then didn’t really use it so I stashed it in the hall closet, just in case.” He shrugged, “I switched out the top part. I mean, I remember the vibration being pretty strong. You, uh, you could use it – to help.”

 

Dean swallowed thickly, mouth suddenly dry. Fucking Sammy. Oh shit, now he couldn’t think about anything else – stupid adorable teenage brother offering him a better way to get off – fuck. Dean’s eyes rolled into his head just thinking about it. He nodded.

 

Before he could even remove the hand from his dick, Sammy flicked the toothbrush on. Both brothers stared at it. Tilting his head, Sam pressed it to his finger, first with the bristles and then with the smooth plastic on the back. With a quirk of his lips, almost as if shrugging with his mouth, Sam lowered his second hand to the bed.

 

Dean groaned, uncertain, watching as Sam turned more to face him. His younger brother licked his lips and breathed out heavily. Dean’s nerves were tingling and each passing second left him aching, his cock pulsing with need, ass clenching around his fingers. With a flicked glance up to Dean’s face and back down, Sam reached out and angled the brush towards him. Still buzzing, the smooth head of the toothbrush connected with the underside of Dean’s cock, just over Dean’s fist and just under the head.

 

With a choked cry that quickly became a sob, Dean’s back arched off the bed, his eyes rolling shut. As the buzz rocketed through his nerves, Dean’s hips rolled, his fingers thrusting in and out and his fist clenching and loosening around his dick to up the pressure without jerking it away from the sensation.

 

Little hiccupped cries rolled off his tongue, the pleasure so overwhelming he couldn’t stop them. “Cup your balls Dean,” Sam urged, voice quiet so as not to scare Dean away.

 

Blearily, Dean opened his eyes and looked at Sam. “What?”

 

“Just do it,” Sam ordered, his voice a tad more commanding.

 

Dean clenched his jaw but did it anyway, moving his hand away from the shaft and down to cup his balls. Rolling them in his palm, Dean groaned, even as the toothbrush was pulled away. “Sammy?” The name came out as a plea and question all in one, his voice hoarse and clearly exhausted.

 

“Lift’em up a little.” Sam offered a reassuring smile and Dean acquiesced. With his legs spread and balls lifted, Sam had all the access he could want – Dean just didn’t know what for. With a smirk, Sam moved his hand between Dean’s thighs and positioned the toothbrush again, this time against the tender skin just behind Dean’s balls, right over where his fingers were still thrusting inside. The return of vibration was exhilarating and overwhelming. A moan was pulled from his lungs, his chest rising off the bed as his hips drove down, down, harder against the buzzing.

 

“S’ that,” Dean panted. Even incoherent his brother was a pro at understanding him and answered.

 

“It’s your perineum Dean, hits your prostate from the outside. Go ahead and use your fingers too.”

 

Dean stared at Sam wide-eyed, panting harder and more desperate than even before. “Trust me Dean,” Sam pleaded, imploring him with his signature puppy-dog eyes. Dean blinked and swallowed hard, staring back at Sam. He didn't know how Sammy could know these things – little freak always acted so innocent, but then again, he’d probably just researched everything.

 

Tugging his balls, Dean twisted his fingers hard inside himself and with two, three rough passes over his prostate from the inside and the unrelenting vibrations on the outside, Dean’s orgasm punched out of him and over his fingers, spilling in creamy strands over his knuckles and belly, pooling in his navel and dripping down to soak into the blanket under him.

 

As the pulse of Dean’s cock slowed and he sagged blissfully into the bed, Sam pulled away and switched off the vibration. Dean’s chest heaved as he tried to catch his breath, his hands pulling free and dropping to the bed beside him, legs falling flat.

 

Slitting his eyes, Dean peered at Sam still lingering at his side. His brother looked satisfied with himself, cheeks pink, a small smile quirking his lips. Fuck. What in the hell did he just do? Oh fuck. Fuck, fuck, fuck. Dean’s breath caught in his chest, tension choking the air from his lungs. How could he have let this happen?

 

Dean sat up and leaned over his thighs, curling an arm around his stomach and turning away from Sam. Sammy. His fucking 14-year-old brother. Oh god.

 

“Dean?” Sam asked, leaning towards Dean, hand extended. Dean’s eyes flashed in his direction but refused to meet his gaze. He batted his brother’s hand away and clasped the back of his neck, drawing his knees to his chest. He could feel the panic rising. His skin was hot everywhere and his vision was getting blurry and even with the last tingles of pleasure rolling through his veins, Dean felt mildly sick to his stomach. The watching had been bad enough, but actually encouraging Sam, letting him help – that had crossed a line Dean had never even considered.

 

“Dean, come on.” When Sam tried to lay a hand on his arm, Dean snapped.

 

“Stop it Sam! Get out.” It was a command – no question. And as always, Sam ignored it. Why couldn’t he ever just listen? Dean clenched his jaw and forced himself to meet Sam’s eyes. “This,” he said gesturing between them, “this can’t happen again.” He paused, gaze hard. “You got it Sam? Never. It’s not okay. It’s not fucking okay…and you need to get out – now!” The last word was a shout and Dean could feel the tears gathering behind his eyes.

 

He saw Sam flinch and his eyes cloud with tears, one trickling down an ashen cheek before Sam furiously wiped it away with his arm. His brother glared at him, mouth curling in a snarl but no words coming out. Sam stood, hands curled into fists at his sides, one still clutching the toothbrush. Without a word, Sam stalked to the door and then with all the rage Dean knew his brother was feeling, he chucked the toothbrush right at Dean and ran out of the room, slamming the door behind him.

 

Dean felt the tears spill over, hand dropping to rub his leg where the hard heavy plastic had smacked into his bone. He knew there would be a big purple bruise there – would probably last for days. Served him right. He’d half expected Sam to fight him on this, shout back at him and argue, but this was better – maybe.

 

Cheeks wet with tears, Dean bent over his knees and just sobbed, shakes and shivers wracking his whole body. He felt chilled now, skin clammy in the cool air. Goddammit! What was he supposed to do now?

 

The rest of the house was silent and Dean knew this afternoon had the potential to destroy everything good between he and his brother. Slumping into the blankets, Dean tried his best to breathe through the tears and ignore the sharp pain in his chest. He wasn’t successful, just eventually exhausted himself enough to pass out.

**Notes for the Chapter:**

> I thought I was doing so well writing a story without plot…and then this happened. The angst and feels exploded and I couldn’t stop them. Oh well…more to come!


	5. Chapter 5

**Notes for the Chapter:**

> Despite my intentions to update this story fairly regularly, all of the work for classes this semester had to come first. My deepest apologies for the long break between chapters, and thank you to all of the people who have left kudos, commented, or bookmarked up to this point! I’m extremely grateful! Unfortunately the chapter is a short one and more backstory plot than smut, but not to worry – the smut will return in chapter 6. Enjoy!

By the time Dad came home a few days later, Sam still wasn’t talking to Dean. Dean had tried to act normal, crack a joke, ask Sam about his school day, but every time he was met with a blank stare and clenched jaw. Each time left a bitter taste in the back of Dean’s throat and left him feeling increasingly hopeless. His coworkers at the mechanics had even commented on it the day before, unrelenting in questioning him until he’d snapped, thrown his grease towel at the workbench and stormed out. They all gave him a wide berth until the end of the day.

 

Now with Dad home, the silence had become more obvious, Sam’s usual cheer and chatter glaringly missing and Dad kept shooting raised eyebrows at Dean until he couldn’t take it anymore and disappeared outside to the Impala. The smell of old leather soothed his frayed nerves and Dean leaned back against the seat with his eyes closed, breathing deeply until his heart rate slowed.

 

Just as he was about to flick on the tape player to occupy himself for awhile, the passenger door squeaked open. Dean lurched out of his slouched position, shocked as his father dropped into the seat beside him. Sitting rigidly in his seat, Dean waited.

 

Another slam of the door and Dean was sealed in with his father, the anticipated tension already pushing his pulse faster. “You want to tell me what’s going on between you and your brother?” His dad’s voice was gruff but kind, honest curiosity and worry.

 

Dean wished with everything in him that he could just tell Dad everything, curl up in his arms like he did when he was a toddler, before the fire and losing his mom when everything changed. Maybe if the situation were different he would have, but with this…there was nothing he could say.

 

Dean shrugged his shoulders and peered out the window. “Dean.” Dad’s voice was shorter this time, less patient, and Dean knew he would quickly grow tired of the evasion and get angry.

 

“There’s nothing to tell Dad.”

 

“Bullshit.”

 

Swallowing thickly, Dean eyes stung and he blinked to keep the rising tears back. “So he’s a little angry with me. He’ll get over it.”

 

“It’s been days Dean, and I doubt this started _after_ I got back. Sammy never stays mad at you this long.”

 

“Yeah, well he’s getting older – guess he’s getting more stubborn too, but you already knew that,” Dean bit out. The instant the snipe left his mouth, Dean regretted it, but he didn’t take it back, knew that it would get Dad off his back.

 

For once though his dad seemed to reign in his temper. “You want everyone angry at you, I can arrange that. Otherwise, cut the attitude.” Opening the door, Dad climbed out of the car, bending over at the last second and leaning back into the open space. “Fix it Dean. He can be mad at me all he wants, but you boys need to lean on each other. Got it?”

 

The gruff command reared Dean to attention, his head nodding in affirmation, gaze meeting Dad’s on instinct. Dad nodded and shut the door, going back into the house and leaving Dean to stew.

 

Dean remained in the car for a while after, tapping out the bass-line of the current song on the steering wheel until his fingers were sore and it was nearing dusk. He closed his eyes and swallowed, pushing himself up and out of the car. His chest felt tight and no matter how many deep breaths he took he still didn't know how to fix things between him and Sam.

 

They all sat down to a tense, quiet meal, the only sound in the room the clink of utensils on plates. John periodically shot looks at Dean, lifting a pointed eyebrow until Dean nodded. Satisfied, John took his plate to the sink and snagged a beer out of the fridge. “I’ll leave you boys to take care of the dishes,” he said, exiting the room and leaving an even thicker tension behind him.

 

Dean rose and started on the dishes, soaping and rinsing in a rhythm until Sam appeared at his side with his own plate in hand, an impatient sigh gusting over Dean’s neck. Dean opened his mouth to speak but no words came out. He didn’t know how to fix this or what to say to even lessen Sam’s anger at him. Dammit.

 

He tried again. “Sammy,” he whispered, sensing his brother tense behind him, “I’m–I didn’t mean to screw everything up.” With suds covering his hands, Dean brought the back of his arm to brush his face, swallowing thickly. “I didn’t mean for you to see anything and I never meant to encourage something that can’t happen.” He angled his body at Sam, but kept his gaze at a halfway point, unable to meet his brother’s eyes. “You know it can’t – don’t you? It’s wrong Sammy. We–”

 

“I get it,” growled Sam, thrusting his plate onto the counter with a crash. Dean felt his chest constrict, all of his air caught without means of escape. Just as Sam turned to stomp out of the room, Dean spun and gripped his wrist, soapy water dripping to the tiles under their feet.

 

Dean stared at him with pleading eyes. “Please Sammy, please don’t be mad. I’m sorry – you know I hate disappointing you.”

 

Sam’s posture relaxed slightly, his eyes softening. “Dean…” he shook his head, “I hate when you do that. You always shoulder everything. Yeah, so I’m kind of mad at you still, but I’m more upset with the situation – and I hate that you’re right about it. Nothing ever works out for us, you know that Dean. No matter what, something is against us and I’m frustrated and yeah, angry. I’m–” Sam shakes his head, bangs flopping over his forehead. He shakes his wrist out of Dean’s hand and squeezes his brother’s arm instead before giving him a sad smile and walking out of the room.

 

Dean stares after him, molars clenching on his inner cheek until the tears he feels biting at his eyes are from physical pain rather than emotional. He sniffs and turns back to the sink, dipping his hands into quickly cooling water. Despite how crappy he felt at the moment, Dean was certain that had gone better than it could have. At least Sam understood – kind of. And it’s not like Dean likes any of this any better. He’d never wanted his brother before this had all started. Until his brother watched him get off the first time, Dean had never once thought of his brother when in a sexual situation, and yet here he was considering it and wanting it and knowing nothing could come of it. How fucked up did he have to be for any of these feelings to be real? He hated this feeling, but at the same time he was thankful Sam understood – because no matter how fucked up they both are, it would be so much worse if Sam truly didn’t understand why Dean turned him away.

 

Dean blinked back the tears until he felt he had better control and when the last fork was scrubbed and set to dry on the counter, Dean willed his feet to move until he could drop back down into his seat at the table. He stayed there until it was late enough to feign sleep, claiming exhaustion.


	6. Chapter 6

**Notes for the Chapter:**

> To all the readers that have expressed interest in this story: Thank you! And I’m so sorry for the extended wait. But on a positive note, this is a pretty long chapter (the longest chapter I’ve ever published!), so hopefully it makes up for the unintended hiatus :) Also, porn. Lots of porn to make up for my absence.

Things remained tense between Sam and Dean for a while after their talk, but John was pleased when he noticed the gradual improvement and gave Dean a clap on the shoulder in acknowledgement. The boys slowly rebuilt the easy camaraderie they shared before all this happened, but Dean avoided making the same crass remarks he used to. It wasn’t the same and rather than feeling empowered or amusing, he felt dirty and deceitful. They avoided the topic of sex and relationships in all forms unless their dad asked specifically and even then they kept it minimal. It was still a sore subject, but their relationship was improving and Dean could not be more grateful that the horrible feeling between them was going away.

 

By the time he turned 19, Dean was more comfortable with himself and though he still hid his sexuality from his dad, he was growing increasingly curious and desperate to have real sex. The substitutes he’d been using were great, felt fucking fantastic, but he knew despite their length or girth, they were nothing like the real thing. He wanted the real thing, wanted it bad, and he was determined to get it.

 

With their dad out on a hunt and Sam always buried in his books now that finals were coming up, Dean knew that the next few days would be the ideal time to make his move. He waited to hear from his dad, to make sure the man wouldn’t be home yet, and then watched Sam until he settled into the books and the zone he sunk into every time he studied. Dean smirked and went upstairs to get dressed. Tonight was the night.

 

Dressed in dark wash jeans that hugged his ass just right and a snug shirt that clung to every muscle, Dean dismounted the stairs, slinging his leather jacket over his shoulders, keys clutched in his fist. Giving them a light toss, he shouted an excuse and a goodbye to Sam before ducking out the front door and jumping into Baby. He could feel the anticipation building, his heart racing, fingers slightly shaky around the steering wheel. There was excitement and nervousness, and a very real understanding that this night could change everything.

 

Having done his research, Dean drove two towns over, far enough away that his dad would never hear about it, and close enough that he could get home to Sam quickly if he needed to. Nestled into the corner of town, clearly distant from its heterosexual sisters, was the gay bar Dean had found online. It wasn’t hugely advertised and from the street there was nothing to remark on the goings on inside, but Dean knew from his searches that the place was fairly popular and didn’t attract too much of a negative crowd. The last thing Dean needed was to get into to fight about his tendencies on the night he was supposed to have sex with a man for the first time.

 

Climbing out of the car, Dean wiped his palms on his jeans and taking a deep breath, strode forward and into the bar, his knees feeling mildly shaky. With all the dates he’d been on and the monsters he’d fought, Dean was surprised by how nervous he felt right now. Inside the doors, he was met with the pulsing bass of dance music and the pungent odors typical of any bar. There was something about that smell that made Dean feel instantly more at home, and yet the sights past the doors instantly returned his nerves, the images of men embracing and dancing with other men, women doing the same. In the corner, he even saw two guys making out in the shadows and while it was exhilarating, encouraging even, it also increased his discomfort, nearly sending him back out the door.

 

Forcing himself forward, he walked up to the bar and slid onto a barstool, reluctantly pulling out his ID when the bartender gave him a skeptical look, the fake apparently passing inspection when it was handed back and he was prompted for his order.

 

Beer in hand, Dean felt significantly more comfortable, but couldn’t yet bring himself to look around. He was fiddling with the label on the beer, picking at the edges until they lifted and then trying to flatten them back out. A knock on the bar to his right told him someone had slid onto the seat next to him and even so close, Dean couldn’t bring himself to look up or say anything. He was turning out to be a real pussy and Dean hated that about himself.

 

The sound of a bottle sliding over the bar caught Dean’s attention and then someone was speaking. “First time?”

 

Dean almost choked on his mouthful of beer, turning to stare in shock and horror at the man next to him. How the fuck had he known? Did he have a neon sign over his head saying “ass virgin”?

 

“W-What?” he stuttered, all of his usual cool confidence gone in the face of this new situation.

 

“I asked if this was your first time out? You look a little green, thought maybe you’d never been outwardly…out.” The man winced at his own wording but seemed sincere. Dean was just thankful that the question hadn’t been what he’d thought.

 

For the first time since the man started talking to him, Dean really looked and was pleased to find that he was attractive, the owner of deep brown eyes and a chiseled jaw, disheveled hair that screamed for fingers to run through it, and muscular arms that were evidently strong if not capable of lifting Dean’s full weight. He bit back a moan at the very thought.

 

Realizing he still hadn’t answered, Dean’s cheeks flushed and he ducked his head, rubbing his hand over the back of his neck. “Uh, yeah, first time. That obvious?”

 

“You learn to recognize the look. Everyone’s got a first time like that. I don’t know if it’s possible to go out that first time and not feel nervous. I was a wreck to be honest.” The guy laughed and Dean joined in, thankful that he understood and wasn’t mocking about it.

 

He stuck out his hand. “Dean”, he offered.

 

The man rewarded him with a wide grin along with his hand and name. “Aaron.” At the meeting of their hands, Dean felt a tingle shoot up his arm, his excitement returning. “You want to dance Dean?”

Dean hesitated. “I can’t really dance,” he said, shrugging one shoulder. He hated how inept he felt, how out of place he was even in this environment, surrounded by people he thought were just like him.

 

“That’s no excuse,” Aaron argued with a laugh, tangling his fingers with Dean’s. “Come on, all you have to do is move your hips, bend your knees to the beat. No fancy footwork I promise.” His smile was inviting and despite Dean’s fear of making a fool of himself, there was also an electric tension under his skin, the intense desire to just be a part of this, to jump in, nothing holding him back.

 

With another blush, and Dean was becoming annoyed with how often that was happening tonight, he nodded and allowed himself to be dragged onto the dance floor, a smile lighting his face as his arms settled around Aaron’s shoulders and he just let himself move. The music pounded in his ears and reverberated in his chest, the vibrations blocking out all his worries and his doubts. Aaron’s hands were pressed into his back under his jacket, the heat of his palms soaking through his t-shirt and into his skin.

 

As they bobbed to the music, weaving together, Dean found himself testing boundaries, teasing the nape of Aaron’s neck, pressing their bodies closer, even rolling his hips every so often. It was completely exhilarating and satisfying to know he had an affect on another man, to feel his hips press right back, and big hands pulling him closer. By the second song, their foreheads had fallen together, hot breaths puffing between them and making Dean’s lips tingle in anticipation. Aaron might have been the first man to approach him, but he was nice and unintimidating, and honestly, this was the best Dean had felt in a long time, so the fact that he really wanted Aaron to kiss him wasn’t altogether surprising.

 

Tilting his head to the right just slightly, Dean stared into Aaron’s eyes and licked his lips. He didn’t feel comfortable enough yet to initiate anything between them, but he figured a little enticement couldn’t hurt.

 

Aaron’s eyes darkened and darting his gaze between Dean’s eyes and his mouth, the man leaned in and sealed his lips over Dean’s. The hot press of lips upped Dean’s pulse and sent spikes of excitement up his spine. He shivered and pressed closer, using his arms to drag Aaron’s neck down towards him. The kiss deepened, a gasp allowing Aaron’s tongue to sweep into his mouth, the hot slide of tongues and the press of tongue on teeth raising the hairs on his arms. His hips rocked without his permission, but the return press of Aaron’s body reassured him that he was doing okay and dragged a muffled moan out of his throat.

 

Aaron chuckled against his lips and urged him on, keeping the rocking motion between them as one of his hands broadened its range on Dean’s back, sweeping up to his shoulder blade and back down to clamp around his waist.

 

For never having kissed a guy before, Dean thought it was going pretty well. It was invigorating and despite his nerves, Dean knew he wanted more. This, being held in a man’s hands, having a hard body pressed against his, tougher lips on his own, this was everything he’d been craving since he’d realized his attraction to females was more forced than it should be.

 

When Dean felt his chest aching for air, he angled his mouth away, panting deep breaths against Aaron’s lips. They remained close but allowed themselves to settle back into the beat of the song, swaying and bobbing along with everyone else in the crowd. A grin split Dean’s face and unwilling to appear so virginal, he turned his face away from Aaron.

 

“Don’t hide,” was whispered in his ear, a hand used to direct Dean’s face back at the man in front of him. His cheeks lit red again, but he allowed the adjustment. They finished the song and left the dance floor for a drink, the only interruption they’d had since entering the writhing crowd.

 

Feeling shy but determined, Dean took Aaron’s hand and dragged him back out to the floor, happy when the other man joined him without hesitation and took him back into his arms. They kissed and ground their way through a few songs before something between them shifted, the tension between them ratcheting up a little more.

 

As the current song morphed into another one, Aaron leaned in and kissed Dean’s mouth again, the barest touch before he moved his mouth along his cheek and down his neck. Dean’s head dropped back, an invitation for more, and Aaron gladly took it, lighting Dean with desire and pleasure until he trailed kisses back up to his ear. As their hips pressed together, both of their cocks hard in their jeans, Aaron whispered in Dean’s ear. “You want to get out of here?”

 

Dean forced his head up and locked eyes with Aaron, his excitement and nervousness battling for the upper hand. Taking a deep breath, Dean tightened his grip on Aaron’s shoulders and nodded, biting his lip at the butterflies lashing against his insides. Aaron smiled and took his hand, leading him off the floor and out the main doors. “I’ll follow you,” Dean managed through the thick feeling in his throat, voice deeper than it had been the rest of the night. Aaron shot him a heated look and headed for his car, waiting for Dean to climb into the Impala and follow him home.

 

***

 

Dean pulled the Impala along a side street near Aaron’s apartment building, unwilling even in his excitement to risk his car on a crowded and busy road. As casually as possible, Dean climbed out of the car and ambled down the sidewalk to the front doors, trying his hardest not to look too eager. When he reached Aaron, the man grasped his hip and pulled him in, gracing Dean’s lips with a short but heated kiss before he pulled away and tugged Dean after him.

 

They took the stairs and on the fifth landing, Aaron led Dean into the hallway, stopping to press Dean against his front door for another kiss before opening it and welcoming him inside, the door clicking shut behind them. Suddenly faced with the reality of the situation, alone in a man’s apartment, no other people or music to distract him, Dean felt himself tense, his hands curling into fists and releasing repeatedly as his body registered its fight or flight instincts.

 

Aaron had taken a few steps into the apartment, but turned around when Dean didn’t follow. “Hey man, you okay?”

 

It took Dean a second to register the words and to respond. He offered a weak smile and nodded, taking a hesitant step after the other man.

 

Aaron smiled back, but didn’t try to get closer or touch him. Dean was grateful and inhaled deeply to calm himself. “You want a drink?” Aaron asked, turning into his kitchen without waiting for a response. He reached into the fridge and pulled out a beer, grabbing another when Dean nodded. After popping the tops, the man kicked off his shoes and dropped onto his couch, settling into the cushions before he extended the second bottle towards Dean.

 

Dean swallowed thickly but strode forward, determined not to be a pussy about this too. He wanted this, wanted it bad, so why was being here suddenly so hard? He sat down and took the bottle, allowing himself a long swig and then set it down on his leg, the cold glass forming a wet ring on his jeans. He traced it nervously, refusing to lift his gaze beyond the top of the bottle.

 

Having sat a good foot away from Aaron, the other man leaned forward and cocked his head, trying to make eye contact. Dean stubbornly kept his gaze on his knees. “You second-guessing all this?” The question wasn’t asked unkindly, but Dean flinched anyway. “It’s okay, you know. You don’t have to go through with anything.”

 

Aaron was being so _nice_ about everything it was making Dean hate himself. Why was he having such a hard time with this? He needed to calm down, because from how this night had played out so far, Dean would never be lucky enough to have his first time with someone like Aaron again. Dean’s jaw pulsed and he startled when a finger reached out to soothe it. “Dean…”

 

Dean opened his mouth. “I’m not…second-guessing.” He shook his head, closing his eyes against his discomfort. “I’m not.”

 

“Dean, you don’t have to do anything. You look beyond uncomfortable right now. If tonight’s not the night, it’s okay–”

 

“I want to though!” The words bubbled from Dean’s lips without his permission and he could feel the building frustration forming the ache of unshed tears behind his eyes.

 

“If you’re sure…” Aaron prompted and Dean nodded. “Then how about you try sitting a tad bit closer.”

 

Dean blushed but did as he was told, sliding across the cushions so his thigh met Aaron’s knee where his leg was tucked up underneath him. Aaron smiled and guided Dean’s face to his, a finger under his chin. “Hi,” he whispered.

 

“Hi,” Dean whispered back, feeling himself relax at the kind and patient look directed his way.

 

“That’s better,” encouraged Aaron, settling his free hand on Dean’s knee, his fingers playing at the seam on the inside of his thigh. He kissed Dean’s lips lightly, no heat, and pulled back. “Tell me a little about yourself Dean. Where are you from?”

 

Dean hesitated, always leery of people looking for his life story, but found he trusted Aaron. “I uh, I was born in Kansas, but I kind of grew up on the road, you know? Never really settled or had one place to call home. My dad, he works odd jobs, so me and my kid brother get dragged along for the ride.”

 

“Yeah? Sounds tough. My family moved once when I was a kid and I remember throwing the biggest fit. Turns out where we moved to was actually a lot better for when I came out, a lot more accepting than my hometown.”

 

Dean nodded. “It was hard, still is sometimes, but I gotta be there for Sammy, so I don’t have much choice. I’ve never actually come out though so where we are doesn’t really matter.”

 

“Never? Not even to your family?”

 

“Especially not to my family. Well, not on purpose. My brother knows now, but my dad, if he ever found out…”

 

Aaron nodded with understanding and stroked Dean’s cheek. “You’re brave then, coming out tonight, taking that risk.” Dean offered a weak smile. “You are,” Aaron insisted and then leaned forward and pressed his lips to Dean’s.

 

Dean let himself sink into the kiss, let the real world, his worries, fade into nothing as the heat from Aaron’s mouth settled into Dean’s skin and swept over his whole body. He shivered and turned into the kiss, pressing back harder, pushing his tongue forward to get what he wanted. Aaron welcomed him in and setting his bottle down, pulled Dean across his lap.

 

Dean usually wouldn’t let anyone else take control, but the simple fact that Aaron _could_ sent tingles up Dean’s spine, and that was really why being with a man was so much more appealing. A man’s strength was part of what made the attraction so strong.

 

Dean settled his knees on either side of Aaron’s hips and wrapped his arms around the man’s shoulders. Tangling his fingers into the hair at Aaron’s nape, Dean pressed harder into the kiss, allowing Aaron’s tongue free reign and giving into the sensations. As the man’s hands swept up his back and gripped him close, Dean rocked his hips down, his ass brushing over Aaron’s cock, his own growing erection confined between their stomachs.

 

Panting, Dean broke the kiss, gasping when Aaron trailed his kisses down Dean’s neck rather than releasing him completely. The wet heat on his skin sent tingles through Dean’s body and his erection throbbed harder, his hips jerking out of rhythm. He moaned.

 

Leaving a wet trail up Dean’s neck and across his jaw, Aaron slid his hands under the shoulders of Dean’s jacket, pushing the leather off and down his arms as Dean pushed closer and harder against him. The moment was thick with heat and excitement, Dean’s nerves combining with pleasure to set his body on fire.

 

As leather dropped between Aaron’s feet on the floor, his hands returned to repeat the motion on Dean’s button up, the fabric sliding from his shoulders and pooling on top of the jacket. The newly exposed skin tingled in the open air, hair rising on his arms. “God, please,” Dean panted into Aaron’s throat, his fingers clutched tight around Aaron’s shoulders.

 

“I’ve got you,” Aaron whispered back, his palms pressed hot against Dean’s skin beneath his undershirt. With a sweeping motion, the shirt met Dean’s ribs and then Dean’s arms were in the air, eagerly lifting to let Aaron remove the last bit of clothing on his upper body. He felt the chill raise goose bumps on his skin and tighten his nipples, the skin puckering against the new sensation.

 

Aaron tugged off his own shirt and with all barriers dropped between their bodies, Aaron claimed Dean’s lips once more, sucking Dean’s tongue into his mouth and near devouring his lips. Dean moaned into the kiss, groaning as large hands caressed his body. When one hand caught on his chest, dragging over his nipple, his breath caught in his throat, exhaling in a whimper when fingers moved to twist the sensitive nub.

 

A breathy chuckle released into his mouth and for a moment Dean tried to pull back, embarrassed by his reaction. “No, don’t pull away. Fuck Dean, you’re gorgeous.” Dean’s cheeks flooded with red, but he allowed Aaron to pull him back tightly against his body.

 

Tongue back in Dean’s mouth, Aaron distracted the younger man until the tension retreated from his shoulders, his hands gradually finding their way to the zipper of Dean’s jeans. In seconds denim was parted and encouraging hands helped lift Dean and pull the pants down past his hips. With a bit of wriggling and uncomfortable maneuvering Dean was relieved of his jeans, settled in only his boxer briefs across Aaron’s lap.

 

Aaron swept his hands over Dean’s thighs, gliding over his skin and cupping his hips, soothing the sudden rise in tension evident in his frame. Dean shivered, a combination of chill and fear. “You okay?”

 

Dean pressed his lips together and nodded against Aaron’s neck, the slight rasp of stubble grating against his cheek. Aaron kissed Dean’s temple, dropping one hand until it rested over the bulge in Dean’s underwear. As long fingers grasped him through cotton, Dean gasped, grip tightening on Aaron’s shoulders. It was unnerving how out of control he felt, immersed in something he knew next to nothing about, unsure how to proceed, how to act, what to do. Dean’s chest heaved with the pressure, panting in a confused mixture of pleasure and anxiety.

 

“Relax Dean,” Aaron murmured in his ear, the hand on his back moving in rhythmic circles, the other continuing it’s gentle exploration through Dean’s boxers. Dean nodded and rocked his hips into Aaron’s hand, groaning when the pressure increased.

 

“Feels good,” Dean managed, biting his lip to hold back the sounds trying to escape. Aaron smiled through the kiss and rubbed harder, focusing his ministrations near the tip, hissing in satisfaction at the feel of pre-come seeping through the material. Opening himself to the pleasure, Dean deepened the kiss, grinding into the sensations on his cock, and dropping his hands to tease at the button on Aaron’s jeans.

 

Breaking the kiss, Aaron grinned at Dean, nipping at his lip before abruptly shifting him sideways off his lap, Dean’s back meeting the couch just as Aaron’s body settled on top of him. Dean sucked air in when their lips parted, a giggle bursting from his mouth as he was tossed to the side. “God, you’re fucking adorable,” Aaron whispered against Dean’s lips, eyes glittering in amusement.

 

Dean’s cheeks flooded with red for the millionth time that night and he struggled to push down his embarrassment, determined to make it through this night without seeming like a child. “Not.”

 

“Mm, but you are,” Aaron insisted, nuzzling his nose into Dean’s cheek before sealing their lips together. As the kiss grew heated again, Dean worked at Aaron’s jeans, shoving at the stubborn fabric until it finally gave and slid reluctantly down his legs. At feeling the older man’s hard length against his own, Dean moaned, the burst of sound swallowed into a kiss.

 

Feeling the desperate need for full body contact, Dean wormed his hand between their bodies, dragging his boxer briefs down. Aaron caught on and first dragged his own off before lifting off of Dean enough to pull his off too. At the sight of Dean’s naked body, Aaron’s breath caught in his throat, his gaze slowly lifting to meet Dean’s eyes. “You’re gorgeous.”

 

Dean averted his gaze, unable to stop himself from taking Aaron’s body in too. As the man’s cock caught his attention, Dean swallowed thickly, struck again by nerves and excitement. Aaron smirked, noticing where Dean’s eyes had strayed and lifted an eyebrow. “Like what you see?” Blood rushed to Dean’s cheeks as his eyes closed, embarrassment overriding all other emotions. Aaron continued, stroking a finger over Dean’s flushed cheek. “I like what _I_ see.”

 

Dean forced himself to respond, to nod, giving some indication that he wasn’t a scared little boy in over his head. But he was. In the way that he had no idea what to do next and he was feeling so incredibly vulnerable he wasn’t sure exactly if he should go through with this or not. His breathing sped up. He wanted this so badly but was it worth the possible embarrassment?

 

Aaron’s voice cut into his thoughts. “Dean, are you okay?” Opening his eyes, Dean licked his lips and nodded, willing words to come out of his mouth this time.

 

“Yeah,” he rasped, “M’good. Want you.” The words were somehow both the most satisfying and terrifying things to ever leave his mouth. He meant them, god did he mean them, but at the same time he was scared of how things would proceed. He’d experimented, sure, but this – the real deal – this was beyond intimidating.

 

A smile crossed Aaron’s face and in the next moment their full bodies were pressed together, naked skin on naked skin. Dean breathed a soft sigh, the weight of Aaron’s body a soothing presence over his tense frame. “Please,” he whispered, “need this. Need you.”

 

“Yeah,” Aaron breathed back into his mouth, hot breath ghosting over Dean’s lips. “Okay.” Aaron claimed Dean’s lips, the older man’s tongue flicking over his palate, gliding over every inch before pulling back. He sucked on Dean’s bottom lip, giving it a slight nip before angling his forehead to meet Dean’s. “Want to move this to the bedroom?”

 

Hot breaths puffed against Dean’s lips, the question spiking something hot and desperate in his blood. His heart was suddenly racing, palms sweating, but there was also a sense of excitement that he couldn’t ignore. Nodding, Dean lifted his face, kissing Aaron again before drawing back and pushing against the man’s chest, rolling his own body from its comfortable position on the couch to get them moving.

 

Aaron laughed, his smile easing some of Dean’s discomfort, as he was tugged into the next room. With the flick of a switch, Aaron’s bedroom was lit by a soft light, his massive bed taking up a large portion of the space. Dean swallowed thickly but allowed himself to be pulled forward into the room. Aaron spun Dean to meet him, their chests meeting just as their lips did the same. Dean relaxed, the familiar motion of tongues and lips weaving together easing him into what was about to happen.

 

As they kissed, Aaron’s hands grazed over Dean’s skin, his caress leaving goose bumps in its wake. Dean shuddered and kissed back harder, lifting up on his toes to reach Aaron’s mouth more solidly. This was the first person he’d kissed where he was shorter than his partner. It was strangely exhilarating and his fingers knotted into Aaron’s hair, the other arm locked around the man’s neck, pulling him closer. Groaning, Aaron wrapped an arm around Dean’s slender waist, bending the shorter man’s body against the curve of his own, his other hand sliding down Dean’s skin to palm over his ass. He cupped the firm mound, pressing, lifting, and Dean gasped at the feeling.

 

He broke the kiss to breathe, panting against Aaron’s mouth. The corner of his lips lifting in a smirk, Aaron dropped the second hand to do the same, pressing Dean’s hips hard against his own, guiding the younger man in small steps to the mattress. Dean allowed himself to be shuffled along, a groan leaving his throat when his knees connected with the bed.

 

Slowly, Aaron pushed Dean down, their bodies landing on the bed with a slight bounce. Dean laughed, his face turned away from Aaron’s even as his arms pulled him closer. Aaron kissed Dean’s cheek, trailing his lips over his jaw until he reached his ear, nibbling the delicate skin there until Dean turned back to face him and locked their mouths together again.

 

Without hesitation Dean rocked against Aaron, his hips lifting from the bed to grind their cocks together, hard flesh meeting and tingling in a way he’d never felt before. Picking up the motion, Aaron ground down against Dean, his hips heavy and skilled. There was no awkward fumbling from the older man, only confidence that comes with experience.

 

As their hips maintained a gentle rocking motion, Aaron’s hand caressed Dean’s sides, the other supporting his weight. Red brushed the surface of Dean’s skin, a heated flush spreading from his groin outwards. Dean moaned breathily, the sound choking off when Aaron’s fingers found his nipple. With a pinch and soothing brush, it pebbled on Dean’s chest, his body arching upwards chasing the blissful sensation. “Oh you like that,” Aaron nearly growled, his voice dropping another register.

 

Dean could only nod, his hands gripping Aaron’s shoulders, tightening when his other nipple was given the same treatment. His whole body tingling, it took him a minute to realize Aaron’s hands had coasted down his body, dropping to circle over Dean’s thighs. Having pulled backwards onto his knees between Dean’s legs, Aaron cupped his hands around the backs of Dean’s thighs, lifting and pushing back so Dean’s knees were angled at his chest.

 

“Wh-what–” Dean started, discomfort causing his voice to shake.

 

Aaron shushed him, offering him a reassuring smile. “I have to prep you, Dean.” He paused, “That okay with you?”

 

Dean flushed hotly. Unable to speak, he nodded, turning his face away so he could stare out into the room instead of looking at Aaron. The older man continued to rub soothing circles into Dean’s legs, reaching out to his bedside table for lube only after some of the tension had dissipated from Dean’s frame.

 

The cap clicked open and Dean knew what to expect, had done this to himself before, but nothing could prepare him for the sensation of someone else’s fingers meeting his rim. He gasped, fingers clutching the sheets underneath him. The finger pressed gently, ghosting over the sensitive flesh, before it finally pushed forward, only the tip entering Dean’s body. Involuntarily, Dean clenched and stopped breathing.

 

“S’okay Dean. You can handle this.” Dean nodded, closing his eyes. Maybe this would be easier if he couldn’t see anything, pretended he was back in his bed at home doing this to himself. The finger pushed deeper and Dean blinked his eyes open. Nope. He could imagine all he wanted, wouldn’t change that he had another man’s fingers pressing into his body. The finger eased deeper, pulling back and pressing inside again, the slow motion repeated until Dean was taking the full length of it, Aaron’s knuckles curled against his ass. “You ever done this to yourself?”

 

Dean panted, nodded. “Ever used more than one finger?” He nodded again. Aaron seemed to consider that and smiled, his thumb rubbing in circles at the back of Dean’s right knee. For a few slow minutes, Aaron continued the back and forth motion of his finger, pulling out only to add more lube and attempt a second, then finally a third.

 

Dean had never felt more awkward than having his legs in the air and another man’s fingers inside him, but at the same time there was a sense of calm and satisfaction at finally having what he’d wanted for so long. The fingers curled and Dean’s back arched, his hips pressing down into Aaron’s hand, seeking out the intense pleasure he’d felt moments before. He groaned, rocking his hips down harder. “Almost there Dean. That’ll be even better soon.” Dean finally met Aaron’s eyes and groaned, knuckles turning white where they gripped the sheets. Aaron chuckled.

 

After a few more thrusts inside, Aaron pulled his fingers out, the squelching sound loud in the room. Dean winced and closed his eyes, hoping desperately that Aaron hadn’t heard the embarrassing sound. In all his experiences with women, similar sounds had never phased him, but the fact that it came from his body left him feeling extremely vulnerable, too open and unprotected in the presence of the older, larger man. Aaron’s weight shifted on the bed, the grating of wood on wood signaling the opening of a drawer.

 

Dean heard the familiar rip of foil in the otherwise silent room and held his breath, suddenly unsure if he could go through with this. A soft touch grazed over his knee, easing his legs down into a more relaxed position. The hand moved to his face, cupping his jaw. “Dean?” Dean swallowed thickly, unable to answer. “Dean, you have to breathe hon.” The little air in his chest released, his lungs suddenly desperate for more. “Look at me, Dean. Are you okay? Do you need to stop?”

 

Forcing his eyes to open, Dean met Aaron’s concerned gaze. Aaron was showing endless restraint and patience and Dean couldn’t help feeling ridiculous that he was being so difficult. “Dean?” Aaron pushed for an answer.

 

“I’m good,” Dean rasped, throat still tight. “Really.” Feeling awkward but determined, Dean reached out to Aaron’s shoulder, sliding his hand behind his neck to pull him into a kiss, and showing more confidence than he was feeling, Dean wrapped his leg around the man’s hip, urging him down on top of his body.

 

“If you’re sure,” Aaron murmured into Dean’s lips. Dean nodded and rocked his hips. With a groan, Aaron pulled back and slid the condom onto his cock. Dean watched with rapt fascination, nervous and eager to have that inside him.

 

Aaron lubed his cock and adjusted Dean’s legs, easing the way for his body between them. Dean panted, eyes wide in wonder as the swollen head met his rim. With a bit of pressure, the head was in and Dean’s head dropped back on his pillow, open-mouthed. The pressure was similar to that of his toys, but the heat and pulsing thickness was totally new. Aaron pressed slowly inside, Dean’s legs wrapped around his waist, eagerly encouraging him deeper. This was so much better than any toy.

Dean moaned, fingers clutching at Aaron’s shoulders, at the back of his neck, pulling him closer. He felt so full, and the feeling was foreign but exhilarating and Dean turned his face into Aaron’s neck, kissing the skin there wetly. Aaron turned to meet him, their breath puffing hot between scorching kisses. After easing his way in for a few long minutes, Aaron rocked his hips harder into Dean, the slap of skin loud in the air. The sound was punctuated by a breathy gasp from Dean’s throat, the sudden depth of Aaron’s cock inside him startling and oh so good.

 

Distracted by Aaron’s kisses, Dean didn’t notice right away that the older man’s arms had moved from their position by his head. It was only when his hips were suddenly angled higher in the air, Aaron’s forearms sliding under his thighs that Dean realized something had changed. Aaron adjusted their bodies, settling Dean’s knees over his shoulders, leaning in until Dean was bent nearly in half. There was a moment of panic accompanied by bliss, the new angle lining Aaron’s cock up with his prostate. Tingling pleasure raced up Dean’s spine, his breath caught in his chest. It was almost mind-numbing how much pleasure that one little part of his body could give him.

 

Aaron’s hips kept their rhythmic pattern, slamming inside him with increasing power. Dean’s neck strained back, his lungs fighting for air. He had never felt something so good, never wanted anything to last so much, and yet there was a niggling feeling, something keeping him from giving in completely to the sensations.

 

As good as he felt in the moment, he couldn’t help the instinct ingrained in him since age four to always have a way out of a situation. His father had been persistent, always know the exits, always have a way out. And from his position under Aaron, legs in the air, Dean knew he’d have a hard time escaping if he needed to. The chances of needing to get out were slim and yet Dean was feeling increasingly powerless and out of control.

 

Dean shut his eyes, gasping, arms caught between pulling Aaron’s shoulders closer and pushing him away. He felt such a mix of sensations and emotions, his legs twitching with the instinct to move, to get out of the restraining hold, and yet his hips twisted, pulling Aaron deeper inside, begging him closer. Despite his niggling misgivings, Dean could not bring himself to pull away, could sense how quickly he was about to lose control. Aaron lifted a hand to cup Dean’s cheek. “You okay?”

 

Panted breaths were Dean’s only answer, teeth pressing white lines into his lip, eyes fluttering, near rolling back into his head. He whimpered, attempting to nod even as Aaron’s hips grew faster and pleasure zinged up Dean’s spine. He could feel the growing heat in his belly. Aaron chuckled through his own heavy breathing, kissing Dean’s cheek and lingering there as his hips missed a beat, becoming erratic as the older man too neared his orgasm.

 

Aaron’s hand traveled down Dean’s side, sending shivers over his skin, and settled over Dean’s hand, which had twisted itself into the sheets below. Weaving their fingers together, Aaron moved Dean’s hand to rest by his head. “Think you can come without a hand on you?” His mouth was lifted in a smirk, eyes lit with both pleasure and his apparent anticipation.

 

Dean’s face scrunched, the pleasure overwhelming even as he doubted his ability to follow through on Aaron’s request. He shook his head but pressed his hips up, lifting, twisting, anything to feel that thick hot cock press deeper and harder inside him. His mouth fell open in a gasp, a sob escaping alongside it as Aaron’s cock pressed insistently against his prostate.

 

“S’okay sweetheart. Come for me Dean.” Dean’s eyes shot open, brilliant green a thin ring around blown pupils. With his limited range of motion, Dean lifted his hips again, meeting Aaron’s thrusts as best he could. His cock throbbed hot between their bellies, pre-come dribbling from his tip, leaving streaks across the skin there. His balls felt heavy, and despite his doubts, he could feel the bubbling heat pressing upwards.

 

He felt the urge to stroke himself, wanted that pressure and heat of his palm, tried to move his hand, but Aaron held firm. “Try Dean.”

 

“Oh god, oh god, oh god,” Dean gasped through swollen lips, fingers curling around Aaron’s where they held him to the bed.

 

Three more deep twisting presses inside and Dean’s back arched clear off the bed, hips jerking as pleasure coursed in a heat-filled wave up from his belly and outwards to every inch of his body. Sticky wet heat spilled onto his stomach, muscles clamping down, his whole body trembling with the intensity.

 

Through the haze of pleasure and the ringing in his ears, he could hear the murmur of “beautiful”, could sense Aaron’s sharp thrusts, his near desperate pursuit of the same release. Hand still clenched tightly around Dean’s Aaron came, hips pounding erratically for long moments before petering out into softer thrusts, losing momentum until he finally collapsed onto Dean.

 

As Aaron’s weight settled over him, the man maneuvered enough to release Dean’s legs, his knees slipping off of Aaron’s shoulders to splay wide around his hips. Dean again felt the urge to check his surroundings, to be free of his constraints, and yet another part of him wanted to linger in the closeness, revel in the weight of his partner and be surrounded by the hot cloying heat of their lovemaking.

 

And god Dean felt ridiculous for thinking of it that way, but he is fully aware of how this night could have gone, knows other men could have been far more demanding and expectant. He was lucky to have Aaron as his first and though they don’t really know each other, nor will they likely see each other again, he couldn’t help but think this night was just a little more than sex.

 

After a few long minutes of resting together and catching their breath, Aaron heaved himself up and sat back on his knees, caressing his hands down Dean’s sides and raising goose bumps on his quickly cooling flesh. He pulled the condom off and grinned at Dean. “I’ll get a towel.”

 

Dean just blinked at him, his body feeling heavy and tired, his lips twitching in the semblance of a smile. In moments Aaron was back with the cloth, gently easing it over Dean’s sensitive skin. “You enjoy yourself?” He asked softly, the towel sweeping over Dean’s belly and then down between his ass cheeks, ridding him of come and lube and sweat.

Dean’s mouth lifted in an attempted smile, his head attempting a nod but mostly just rolling on the pillow. With the towel balled up in his palm, Aaron chuckled and leaned over Dean, his fists supporting his weight. “I’ll take that as a yes,” he said, leaning in to kiss Dean again.

 

Managing to kiss back, Dean pulled back enough to say, “That’s a hell yes.” Aaron laughed into his mouth.

 

They kissed lazily for a few more minutes but Dean could feel himself fading fast. Knowing he shouldn’t just pass out in this guy’s bed, he tried to sit up.

 

“You can stay,” Aaron offered, his hand curling possessively around Dean’s hip. “I definitely won’t mind having you here in my bed awhile longer.”

 

Dean hesitated, knowing he should go home, but wanting to stay and make a full night of it. He wanted to remember everything about this night and staying would somehow finish off the experience without making him feel cheap. He hoped. Biting his lip, Dean nodded. “Okay,” he agreed, ducking his head as yet another blush flooded his cheeks.

 

Aaron settled on his side next to Dean, inviting the younger man to lay with him. Dean ran a hand through his hair. This was more than he ever could have hoped for. With a rub over the back of his neck, Dean tried to mentally shake off his nerves and lay down. He curled on his side facing Aaron, unable to stop himself from watching the older man. Aaron smiled and draped an arm over Dean’s waist, his fingers tracing unnamed shapes on his lower back. Dean shivered and Aaron pulled him closer, tucking Dean’s head underneath his chin.

 

After a few adjustments and some awkward shifting, Dean was settled comfortably against Aaron’s chest. He almost spoke up, said goodnight, but he didn’t want to shatter the soothing atmosphere just then. He was too content and so he settled for stroking his hand over Aaron’s chest, just above his heart. The gentle motion lulled him closer to sleep and feeling how relaxed Aaron was underneath him, Dean let himself fall under.

 

***

 

Dean blinked awake to dim light, his vision still blurry and his face mushed into a pillow. Not exactly wanting to get up but knowing he needed to get a move on and get home to Sam, he stretched and pulled himself upright. He took a moment to just breathe before he stood and noticed his clothes draped over the end of the bed. A smile graced his lips, happy that even the morning after, Aaron could be thoughtful. The last thing he would have wanted this morning was to have to venture into the open apartment bare-assed because he’d been stupid enough to get naked in the living room the night before.

 

Tugging his clothes on, Dean ambled out of the bedroom to the rich smell of coffee. As he turned into the kitchen he saw Aaron seated at his kitchen table, clad in shorts and a tank, a mug cupped in his hands. “Sleep well?” He asked around the lip of the mug.

 

Dean nodded through a yawn, shuffling into the kitchen. Aaron laughed, lips quirked as if holding back.

 

“What?” Dean demanded, though the gruffness he intended was lost in another jaw-cracking yawn.

 

Aaron gestured around his own head, as if to indicate his hair, “You’re cute with your hair all over the place.”

 

Dean’s eyes widened and he turned tail out of the kitchen to find the bathroom. Standing in front of the mirror, he squeaked, something he hoped to god Aaron hadn’t heard from the kitchen. His hair was standing on end in just about every direction, parts of it mashed to the sides of his head, others sticking out in ways that seemed to defy gravity.

 

He heard Aaron laugh again and turned to find the man leaning against the door jam, mug still in hand. “Like I said, cute.” Dean groaned and dropped his head, hands clamped around the edges of the counter. “S’not so bad,” Aaron consoled, still grinning, reaching out to tug Dean into his arms. Dean resisted for a moment but sagged willingly into the older man’s body.

 

“I look ridiculous,” Dean grumbled. Aaron’s chest rumbled beneath his face.

 

“Nah, just a bit…wild.” Aaron laughed and rubbed a soothing hand over Dean’s back. “Want some coffee?”

 

“God yes,” Dean mumbled, “But my hair first.” He pushed away from Aaron’s chest and gently knocked the man backwards, shutting the door in his face. Aaron’s bark of laughter carried through the wood and Dean allowed himself an answering chuckle at his own expense.

 

Minutes later with his hair in some semblance of order, Dean wandered back into the kitchen, this time more awake. He gladly accepted the steaming mug of coffee held out for him and dropped into a chair at the table. After he’d inhaled a little more than half the cup, he looked up again. “Thanks for all this,” he said quietly, hand gesturing to include everything from the last day.

 

“Believe me, it was my pleasure.” Aaron smirked at him and Dean’s cheeks warmed with blood.   He looked back into his mug and swirled the liquid, more at ease with this man he’d just met than he ever imagined he could be.

 

Dean finished his coffee and walked it to the sink. “I should get going. My brother’s by himself so…” He trailed off, uncertain what to do now. He’d never really been good at the morning after and even though this time he was definitely more the girl in the situation, this was also somehow more important than any of those other mornings.

 

“I’ll walk you out.” Aaron offered and Dean was instantly relieved. He gathered his boots and shoved his feet into them, locating his wallet and keys before heading for the door. Aaron pulled the door shut behind them and walked Dean down to his car.

 

Just before he pulled open the car door, Dean turned back to face Aaron. He offered a half-smile and shifted awkwardly from foot to foot. Feeling uncertain but needing to do…something, Dean lurched forward, using a hand to pull Aaron’s neck down. He sealed his lips over the older man’s and held him there, reveling in this last moment together. Aaron returned the kiss, cupping Dean’s jaw and soothing his jitters with a caress down his back. Unable to breathe, Dean broke the kiss and took half a step backwards. His cheeks were bright red and he knew his freckles were evident in the morning light.

 

“Thank you,” he whispered sincerely and wrapped his arms around Aaron’s waist, tucking his face into the man’s chest one more time. Aaron gripped him tightly, allowing Dean to hold on.

 

“You’ll be okay, Dean. You’re brave, remember that.” Dean smiled into his chest and pulled away. He ducked his head, turning his face away, suddenly unsure. Aaron’s hand appeared near his face and turned it back to face him. “Don’t do that. You’ve got nothing to hide from. You’re gorgeous. Own it.” Dean blushed but managed to keep his face forward and his eyes on Aaron. He nodded.

 

Aaron stepped back and pulled Dean’s door open for him. “Go on now. Your brother’s waiting.” Dean climbed in and turned the key, the hum of his baby soothing him and reigniting his grin.

 

He gave a little wave and revved the engine, his baby carrying him down the street and away from his first.

 

**Notes for the Chapter:**

> Hopefully the chapter was worth the wait! Let me know what you thought :)


	7. Chapter 7

Pulling alongside the curb outside their temporary house, Dean turned the car off and took a minute to breathe. Part of him wished last night didn’t have to end, but he knew this life didn’t allow for that. At least now he knew for sure that he liked being with men, fuck, he loved it. That alone, the reassurance, made the one night with Aaron totally worth it. He grinned at himself and climbed out of the car.

Inside, Sam was situated at the kitchen table, slightly burnt toast half-eaten on a plate next to his books. He turned half-accusing eyes on Dean. “Where were you?”

“Out. I told you last night.”

Sam glowered, his bangs hanging heavy over his eyes. “That doesn’t tell me anything. You could have been hurt and I would never know!”

Dean rolled his eyes and ruffled Sam’s hair. “But I’m not and I’m home, so quit whining.”

“I’m not whining!” Even as his brother negated Dean’s claim, a whine snuck into his tone. Dean laughed and pinched Sam’s shoulder, just at the base of his neck. Sam’s head scrunched over Dean’s hand to fight him off, an irritable, “Dean” huffed into the air.

“Oh come on Sammy. Stop being a bitch.”

Sam glared at Dean, his shoulders tense. “I’m not a bitch, jerk.” He started to turn away but stopped, staring at Dean, his eyebrows pinched like they usually are when he’s trying to figure something out. “You smell weird.”

“Shuddup, bitch. I do not.” He reared back, slightly offended, mostly horrified that Sam noticed.

“Yes you do,” Sam argued, stepping towards Dean.

“Fuck off.” Dean retreated, trying to leave the kitchen.

Sam caught his arm, eyebrows rising when he catches on. “Well fuck.” He stared at Dean and Dean couldn’t bring himself to comment on the language like he usually would. “You actually had sex didn’t you? Like with a guy?”

Dean stared back at Sam, eyes slightly wide. He didn’t know what to do. How was he supposed to handle this? Sam wasn’t exactly glaring, but he didn’t look happy either. His brother was completely unpredictable right now and Dean hated it. Sam stepped back, releasing Dean’s arm. “Well good for you I guess.” The words weren’t mean, not happy either; they were almost bitter, but tinged with a bit of sincerity. Dean didn’t know what to make of Sam’s response and rubbed his hand down the back of his neck.

Dean opened his mouth to speak, but stopped. He didn’t have anything to say. Sam continued instead. “Just…make sure I know where to find you next time…or come home. I don’t like not knowing where you are Dean. At least when you’re on a hunt with Dad you tell me where you’re going.” Sam was staring at the floor, bangs hanging so low Dean couldn’t make out his face.

Rather than try to wiggle out of it, Dean nodded and muttered a quiet “okay Sam”. He couldn’t begrudge his brother’s need to know he’s safe, not in the life they lead. Nodding again to affirm his promise, Dean backed out of the room and went to his bedroom.

***

Over the next few weeks, Dean stayed at home more, trying to spend more quality time with Sam. His fifteen-year-old brother was quite the geek but he could be a good time. Dean went to work whistling on most days, thrilled with his one night of experience and proud of himself for pushing himself out there in the first place, happy too that he and Sam were growing closer again.

Dad had come and gone in the meantime, off on another hunt before either of his sons really adjusted to seeing him again. Luckily he’d left more money and Sam was satisfied with remaining at the same school, but Dean had felt overwhelmingly worried that his father would somehow know that he’d slept with a man. He felt like he’d been holding his breath the entire time his father was back, only feeling the pressure recede once the man left again. 

Part of him felt guilty, for acting on his desires and for hiding them from his dad, but a larger part of him just wanted it again. He tried to satisfy the ache at night sometimes, sneaking into the bathroom after Sammy fell asleep, riding his fingers while kneeling on the tiled floor, but there was only so much his knees could take and only so deep his fingers could go. It was too much of a risk to bring his makeshift toys out while people were home, especially Sam at this point, and each night the need grew bigger.

Some afternoons he was able to sneak home after work before Sam got back, use the brush handle or even the flashlight shaft to get himself off, but those days caused him a lot of stress between the anticipation, timing things right, cleaning up, and airing out their room. He needed something and he needed it soon.

After another night of desperate fingering and stifled moans, Dean decided it was time he went back to the bar. Chances were he wouldn’t see Aaron and as good as the time was that they spent together, Dean knew he couldn’t form attachments; it couldn’t happen again.

The following Friday Dean told Sam he was going out, telling him the town and the general area but not where exactly. Sam pressed, but Dean remained tight-lipped, feeling awkward about sharing the information with his baby brother, his potentially jealous baby brother at that. With a huff, Sam relented and waved Dean out, with a “be careful, no, I’m serious Dean”. Dean grinned and climbed into Baby, eager to be on his way.

Sitting outside the bar in the Impala, Dean was nervous and jittery again, his palms sweating and his knees feeling weak. Somehow Dean was feeling more nervous now than he had last time, pulse thumping a racing beat he swore someone else would be able to hear. Forcing himself to move, Dean dragged his palms across his jeans and heaved himself out of the car, pushing himself through the front door before he could second-guess himself.

Once again the music beat a pattern into his chest, pressing around him and again, Dean headed straight for the bar, sliding onto a stool. He needed some liquid courage to bolster him before doing anything else. The bar tender was different this time and just like the time before, Dean was asked for his identification. Luckily, it passed again and his ordered beer was slid across the surface to his fingertips. The biting cold of the glass was familiar and a comfort at the same time as it reminded him what he needed it for and sent an extra beat of anxiety through his nerves.

Unlike last time, Dean was able to finish his drink before anyone approached him and he was feeling much more relaxed when he turned to face the crowded dance floor. He slouched on his stool, propping an elbow onto the bar behind him, his second beer secure in his hand.

When the next song ended he pushed off the bar and wandered onto the dance floor, hesitant but determined to do this by himself this time. With the new beat in the air, Dean slotted himself into an open spot on the floor and started shuffling his feet. Without a partner he didn’t really know what to do with his hands, and for a seemingly endless minute Dean moved by himself around the floor, awkward and unsure.

Luckily it didn’t take too long for someone to come up, a man slightly taller than him, clean-shaven, eyes bright. Pretty hot. Dean gladly welcomed the man’s hands on his hips and he allowed himself to let go a little bit as he immersed himself in the beat and bump and grind of dancing.

As he let himself get lost in the music and the feel of hands on his body, he felt the tension of the last few weeks start to drain from his shoulders. His partner pulled away and not seconds later, another man took his place, this one slightly shorter, rounder in the face but still attractive. Dean gave the man a wide smile and let the beat carry him.

For a long time, Dean bounced around the dance floor, switching partners every so often, even initiating a dance when he was feeling brave enough, the music a constant hum in his bones and the touch of another man a comfort even as the bodies attached to the touch changed. Dean was enjoying himself more than he thought possible and he reveled in the attention, loving every roll of the hips, glide of the hands, brush of stubble against his cheek.

One of his more recent dance partners had bought him a beer and just as he was finishing his third of the evening, Dean’s current partner was tugged away from him by another dancer on the floor; it seemed they knew each other. He was replaced by another – this man tall, broad-shouldered, and big, more muscle than anything else. His hands, where they fell on Dean’s hips, burned through the fabric of his shirt and enveloped him like none before. They curved around Dean’s hips, fingers reaching up his back, holding him tight, drawing him in, and Dean felt a spike of arousal at the sensation. Fuck, that was hot. All of the underlying arousal he’d been feeling all night suddenly became stronger, his cock twitching in a reminder that it wanted attention, his hole throbbing just at the thought of what a man this size could do to him.

Dean’s green eyes flashed to the man’s face, noting the short-cropped hair, the stubble lining his jaw, and his eyes – a deep brown hooded with want. His lips were turned up in a crooked smile, and Dean instantly wanted to attach himself to them. He held back but couldn’t stop his hips from rolling, his cock pressing into the man’s thick thigh.

Dean groaned and the man smiled more widely, hands cradling Dean’s hips and encouraging them to rock forward again. Dean’s arms were lifted to drape across the man’s shoulders and feeling suddenly brave, he used one hand to pull the man’s neck down. He resisted for a moment and then allowed himself to be pulled, sealing his lips over Dean’s in a hungry kiss. It was strangely exciting to know that if he wanted, the man could resist his pull, but chose to lean into him instead.

A gasp for breath and they parted, the man aligning his mouth with Dean’s ear, stubble dragging over Dean’s cheek and causing goose bumps to raise on his skin. “I’m Gavin.”

Blood was rushing so quickly through Dean’s veins his vision blurred, but he was aware enough to answer back. “Dean,” he managed, breathless.

Gavin took a small step back and continued the roll of their hips. “Nice to meet you Dean.” Dean had to fight the urge to look at the floor, a nervous smile lifting his cheeks as he bit his lip. His hips rolled. Damn, this guy was all sorts of hot and Dean knew if Gavin asked, he would leave with him.

Sure enough, after another song and endless meetings of their hips, Gavin leaned in close to Dean’s ear, stubble brushing over his cheek and sending tingles down his spine. “My apartment’s not too far from here. You wanna?”

Dean bit his lip to hold back the grin threatening to out his giddiness at the invitation. He didn’t do giddy. Giddy could go fuck itself. He needed to cool it.

He nodded into Gavin’s neck and tugged on his belt loop, stepping backwards to lead the man off the dance floor. The larger man gave a husky laugh and followed Dean, his big hands clamped over Dean’s hips, guiding him around human obstacles.

***

This time Dean didn’t let nerves get the best of him. He followed Gavin home and stepped right into a kiss once the door locked behind him, letting his brief experience make him cocky and sure of himself. He knew he wanted this, and having done it before he felt more comfortable doing it this time.

Pressed with his back to the door, Dean arched his body into Gavin’s, hands gripping the older man and pulling him close, one hand on the back of his neck to keep their lips moving together. Dean quickly lost his jacket and his button-up to the floor, shrugging out of the layers and pulling off his t-shirt as Gavin’s hands lifted the fabric. He panted against the man’s lips, eyes bright and eager.

Gavin’s shirt was completely unbuttoned, his chest open for Dean’s hands to touch. He was hairier than Aaron had been, definitely more than Dean, and there was something about it that made Dean hot all over. It was all masculine. Hairy. Hard body. It wasn’t long before Dean’s belt was being unbuckled and a huge hot hand was curling around his cock through his boxers. He gasped, head dropping back against the door. Now, now, now pulsed in his head in time with his cock. He fucking needed more.

Seeming to know what Dean needed, Gavin squeezed Dean’s cock one more time and pulled away, settling his hands back on Dean’s hips. He gripped his sides and slid his palms to Dean’s lower back, dropping to cup his ass as he nuzzled a kiss under Dean’s ear. As strong hands seemed to pull and lift at the same time, Dean allowed himself to be moved, upper back pressing harder against the door as his legs shifted to wrap around Gavin’s waist. Fuck, he’d never been manhandled so thoroughly before. It was so fucking hot, that show of strength a definite part of his attraction to men. He groaned and sought out Gavin’s lips, hungry for more, for harder, right now.

Supporting Dean’s weight with a palm under his ass, Gavin adjusted his stance and moved them, the apartment around them a blur until Dean felt the angle shift and suddenly he was on his back, mattress below him. Stubble rasped over his cheek and Dean panted as he pushed Gavin’s shirt from his broad shoulders. He wanted more skin.

In seconds Gavin’s shirt was on the floor and Dean rocked his hips, pressing up in the hopes of pressure on his cock. The older man’s chest was dusted in hair, his muscles appearing to roll under his skin with each movement. Dean couldn’t help but run his hands over them, stunned by how turned on he was by the masculine display. From the mag he’d been making do with since he first got his hands on it, Dean was used to the sight of hairless, muscled bodies, more lean than bulky, and he hadn’t thought much beyond that. Turns out he was missing out on a whole lot. This hard body above his, hairy and thick with muscle was pushing every hot button he had.

He groaned and arched his back, his head dropping to the side, neck stretched out in an enticing line. Gavin gave a low growl at the sight, biting kisses into Dean’s throat as calloused fingers brushed and plucked over nipples peaked in the open air. A whimper broke from Dean’s lips and he turned, seeking Gavin’s mouth.

Lips sealed over Dean’s and seemed to consume him, hands working to undress them both until they were pressed skin to skin from mouth to toes. Gavin positioned himself between Dean’s thighs, hips grinding against Dean’s, the pressure driving him crazy, cock twitching against his belly.

The drag of stubble on his cheeks sent tingles down his spine and Dean knew he wouldn’t leave tonight without tender skin, the burn something to remind him of this night over the following days. He shivered and sighed into Gavin’s mouth, fingers grasping at wide shoulders, pulling, pressing, anything to get closer, move this along faster.

Gavin pulled back and adjusted Dean’s body, tucking his own knees under Dean’s hips, sliding heavy palms up the backs of his thighs and pressing, legs opening wide to reveal his hole. Dean panted, eyes wide as he was laid bare for Gavin’s greedy gaze. Dan felt so exposed and part of him wanted to fold in on himself, embarrassed, yet the position was also turning him on so much he could feel heat bubbling in his stomach.

His knees were angled towards his shoulders, hips lifted from the bed and Dean could do nothing but pant and grip the sheets. Gavin smirked at him. “Hold your legs,” he ordered. Dean’s breath caught in his chest but he did as he was told, lifting his hands to curl behind his knees, pulling them towards his shoulders. “Good boy.”

Dean moaned at the praise. Not seconds later, Gavin’s hands coasted over the skin of his legs, raising goose bumps in their wake. Staring Dean in the eye, he grinned, and then teased his thumb over the wrinkled flesh of Dean’s hole, massaging at the skin, gentle pressure sending sparks of pleasure through Dean’s body. The thumb dipped inside and Dean mewled, eager to have more, needing more. He needed it so bad. Please, please, oh god, now.

Seeming to respond to Dean’s thoughts, Gavin pressed his other thumb to Dean’s hole as well, using both to pull him gently apart. The man’s pupils were blown wide, his own breaths short, exciting Dean that he could affect someone else in this way.

“Such a pretty hole,” Gavin husked, “So eager for me.” Dean’s eyes rolled back in his head. Fuck that was hot.

The thumbs were pressing more, dipping inside him further, pulling him apart. Dean’s eyes shot up to meet Gavin’s at the sudden sensation of cold air. He was met with the sight of Gavin bent over his ass, mouth pursed to blow cold air over his opening. Dean’s hips rocked without his permission and he couldn’t tell if it was to get away or because he wanted more. It was so strange, but also felt unexpectedly good.

A breathy chuckle acknowledged the movement of his hips and then Gavin spat, hot saliva dripping where cold air had just settled. Dean couldn’t tell if he was grossed out or more turned on than ever, knew it would lead to the more he had been craving, and his cock jerked.

With spit easing the way, Gavin’s thumbs pressed deeper and even as they pried him apart, Gavin ducked down to flick his tongue into the open space. There was wet heat, so good, and Dean whimpered, overwhelmed by the intensity. “Such a desperate little hole,” Gavin growled. His tongue swirled around Dean’s furled skin before plunging inside, flicking over Dean’s insides and sending uncontrollable shivers through his frame. Dean shuddered and couldn’t fight the way his hips ground into the hot mouth.

As Gavin’s tongue flicked and swirled over his most sensitive of places, whimpers broke free from Dean’s mouth. He couldn’t control it, couldn’t keep his head from rolling side to side, couldn’t stop the tremble making its way from his toes upward. Stubble rubbed over his skin in stark contrast to the smooth glide of Gavin’s tongue. The different sensations only ratcheted Dean’s pleasure.

When Dean didn’t think he could take anymore without losing his mind, Gavin retreated, giving one last swipe over his hole and up the underside of Dean’s balls and cock. His hole twitched, desperate to be filled as his cock spilled pre-come over his belly. Gavin dipped down to lick that up too before pressing down over his body to seal their mouths together once more.

Dean moaned into the man’s mouth, his fingers slipping in the sweat gathered behind his knees. He heard a grinding and rustling sound near his head and as Gavin pulled back, Dean realized it had been the sound of a drawer opening to retrieve a condom and a bottle of lube.

With his hips still lifted over Gavin’s thighs, Dean was finding it harder to draw in full breaths of air. His chest heaved. Part of him wanted a break to be able to breathe fully. Another, stronger part just wanted Gavin inside him already.

Slick fingers were inside him without warning and robbed him of his breath. They plunged deep and twisted, coating him with lube and stretching him for the wider girth of Gavin’s cock. And it was wider, far bigger than three or even four fingers would be. Even with stretching, Dean would feel the burn of Gavin entering his body. He groaned, heat licking over his body, settling in his cheeks and in the tips of his ears.

After minutes of stretching, deep strokes of Gavin’s fingers and one flick over his prostate, Gavin pulled his hand free and dragged his soaked fingers over the sheets. Dean watched him tear the foil packet of the condom and roll it over his cock, his panting becoming more labored as the moment he’d been desperate for the last few weeks drew closer.

Gavin leered up at Dean and rocked his rubber-covered cock against Dean’s hole. The drag of hot flesh over his throbbing center made his hips rock forward, legs fall farther apart. “Please, please, please,” he chanted under his breath.

“Such an eager cock slut,” Gavin husked, sounding like he’d swallowed gravel. Dean’s eyes shot wide at the dirty turn of Gavin’s words and he mewled again, hips twitching higher. “So good for me, Dean, so needy,” Gavin continued as he lubed his cock, positioning the head at Dean’s hole.

Dean couldn’t control the whimpered “please” that tripped over his lips. He was in a fog of desperation and pleasure, so turned on his eyes were glazed and rolling back into his head.

“Don’t worry, I’ll give you what you need.” True to his word, Gavin pressed forward and the head of his cock split Dean open. His hole stretched wide around the new intrusion and heat spread up his spine, the loud squelch of lube and skin sending a vibrant blush to his cheeks.

Dean’s mouth dropped open in a silent moan, eyes rolling back as he was filled by hot hard cock. Fuck, so good. So good. In one long slow glide, Gavin was inside him completely and he waited, poised above Dean as he let him adjust. The burn radiated from Dean’s hole to encompass his whole body, the feeling a mixture between familiar pain and a pleasure he wanted more of.

As the burn receded, Dean twitched his hips, adjusting the hold on his legs to accommodate Gavin’s body between them more easily. The man shifted to settle more fully on top of Dean’s body, a moment of panic settling over Dean as his legs and airways were restricted. The panic was quickly overwhelmed by intense pleasure, Gavin’s cock grinding against his prostate as he rocked forward, a needy whine spilling over Dean’s lips, biting his bottom one in an attempt to quiet the sound.

“Such a slut for my cock,” Gavin rasped, hips beginning to speed up, gliding deeper and increasingly harder on each stroke. His lips twisted in a pleased grin at each whimper, whine, and moan that he wrenched out of Dean.

To gain better leverage, or so Dean assumed, Gavin sat up on his legs, hands pressing against Dean’s thighs, keeping his hips lifted from the mattress as his own hips thrust forward. He plunged deep, twisting and circling his hips, grinding hard against Dean’s prostate until Dean was gasping at the sensory overload. He pulled back and began a steady rhythm of filling Dean up before drawing back until just his tip remained inside. Dean was near sobbing at the sensations, overwhelmed by the intensity, and even more at how fully he was restrained.

Without any binds in sight, Dean was unable to move, Gavin’s weight and hands strong enough to keep him in place with little effort. There was a part of Dean tingling with pleasure at how completely out of control he was. There was another part that was raising alarms, waving red flags in his mind’s eye that warned him of potential danger. Thoughts of more and get out warred in his head, even as his hips drove up to meet Gavin’s, eager to be filled and owned.

For the moment Dean ignored the warnings, too intent on the pleasure radiating through his body to pay them any mind. “Such a tight fucking hole. So desperate for my cock. Fuck.”

Dean howled at the words, his hole clamping down on Gavin’s cock. The larger man’s hand came down in a slap on his ass, for pleasure or warning Dean couldn’t tell. In any case it had driven a spike of sensation right to his cock, a sticky line of pre-come dripping and connecting to his belly.

Growling low in his throat, Gavin pulled back, this time slipping free of Dean’s body. “No,” whined Dean in a voice he’d later realize was completely embarrassing.

“Don’t you worry little cock slut. I’m not done with you yet.” On the last word, Gavin pulled Dean’s hands from behind his knees and gripped his hips, lifting and turning him in a swift motion that put Dean on his knees. He groaned at being manhandled.

With his face suddenly in the pillows, Dean felt blood rush to his cheeks, a mixture of embarrassment at having his ass so exposed and a feeling of intense arousal. “Fuck,” Gavin groaned, thumbs prodding once more at Dean’s hole, thumbing over the gape and dipping inside. “’S winking at me. So fucking desperate.”

Dean buried his face in the pillows, caught between the desire to press his hips back into Gavin’s fingers and suffocate himself in the fabric. Just like his first time with Aaron, the experience was a constant battle between insane bouts of arousal and overwhelming embarrassment, though this time it was for somewhat different reasons.

Thankfully the decision was taken from him and Gavin secured one hand around Dean’s hip, the other guiding his cock back into Dean’s hole. The new position sent whole new sensations through Dean’s body and he whimpered, his prostate suddenly under constant attack as Gavin thrust deep inside. His mouth dropped in a silent scream, drool falling from his lips as his body convulsed around Gavin’s cock.

Thick hands held him in place as the seemingly enormous cock pounded inside of him, one hand resting solidly in the center of his back, keeping his upper body pressed to the mattress. His body was rendered immobile whether he chose to move or not, the most he could do was press back into the thrusts, maybe twist his head where it lay on the pillow. Other than minor movements, Dean was left simply to take it and enjoy the spikes of pleasure that spread through his body.

Each thrust forward punched the air from Dean’s lungs, short breathy “ah”s punctuating the rocking movements of his body. Gavin kept a hard pace, grunts sounding over Dean’s head, the slap of his thighs and balls on Dean’s skin loud in the room.

Dean curled his hands in the sheets, biting his lip to stifle the sounds that wanted to escape, but found he couldn’t keep them back, the pleasure of Gavin’s cock sliding over his prostate too good, his brain too clouded to remember to be quiet.

He could feel the pleasure building, swirling low in his belly, radiating up through his spine, his legs trembling, mostly relying on Gavin’s tight grip on his hips to hold him up. Dean writhed in Gavin’s hold, mouth falling open in a drawn out moan as he sensed his orgasm getting closer. “I-I need,” Dean whimpered through a moan, “oh god, need more.” He didn’t really know what more meant just then, only that he needed something, just that little push farther to drop him over the edge.

Gavin snarled and seemed to somehow clamp his hands harder around Dean’s hipbones, leaving what Dean knew would be finger-shaped bruises as a memento of this night. Dean’s breath caught and then left him in a near scream when calloused fingers tweaked a nipple, the sensitive nub suddenly caught in a harsh and twisting hold. So, so good. Fuck, dammit, he couldn't take anymore.

One last flick over Dean’s nipple and Gavin’s hand journeyed back down, this time to curl around Dean’s cock, hips still slamming hard against Dean’s ass. Dean shuddered. “Gonna come for me little slut?” Dean muffled a cry into the pillow, knuckles white where they gripped the sheets. “Gonna come?”

“Yes,” Dean hissed, “yes, yes, yes, yes.” It became a chant that followed the quick glide of Gavin’s hand on his cock and the slide of his cock into Dean’s body. Dean could feel a flush spreading up his chest, sweat thinly coating his body, balls heavy, his cock leaking in Gavin’s grip, more than ready to spill.

With a sharp twist and grind of his hips, Gavin drove inside again, and again, his thumb circling the head of Dean’s cock and rubbing just the right spot. Dean’s whole body throbbed and then he was shaking apart with a sob, body curling in on itself even as he pushed back to get Gavin inside him as deeply as possible, cock twitching and streaming hot sticky streaks over Gavin’s fingers, his stomach, and the sheets. His vision went white and he was aware of little else except for the pleasure pulsing through his system and Gavin who continued to thrust, his strokes more erratic until finally Dean felt him tense behind him, hips giving short pumps until he stilled completely. 

When Gavin pulled free from his body, Dean whimpered at the sudden emptiness and collapsed onto the mattress, the supportive hold on his hips then gone as well. There was a wet sound behind Dean, what sounded like the condom being removed. Then Gavin groaned and gave Dean’s ass a light slap, rolling so he landed next to Dean on the bed.

Dean jumped at the slap, but settled quickly, his body boneless and thrumming with the receding pleasure. As his pulse slowed and the ringing in his ears petered out, Dean moaned loudly into the quiet room, “Fuuuck.”

Gavin barked a laugh. “Enjoy yourself then?”

“Enjoy – I can’t feel my legs,” Dean groaned back. Gavin laughed and patted his ass, then trailed a finger between his cheeks. A shudder wracked Dean’s body.

After another few minutes of lying motionlessly on the bed, Dean attempted to sit up on his knees. His limbs still felt shaky, but it was time to get going. No need to agitate Sam by being gone all night again. 

“I gotta get going man, but fuck, what a night.” It still seemed like his voice wasn’t all there and Dean winced at how weak he sounded.

Gavin leaned up and thumbed Dean’s nipple, grazing one last kiss over his swollen lips. “Maybe I’ll see you around Dean,” he offered, more a polite parting than any real offer to see each other again. Dean was grateful that so far he’d met such nice guys. As different as they were, they’d both more than satisfied his needs and both had been respectful of how he was feeling. He grinned and slid off the bed, gathering the clothes he’d discarded in the room and pulling them on.

“See ‘ya ‘round, Gavin,” Dean said through a crooked smile and then left the room. He donned the rest of his clothes and then slipped out of the apartment as silently as possible.

Out in the hallway, Dean ran his hands through his hair, trying to bite back the grin threatening to split his face. Hell yeah!

**Notes for the Chapter:**

> Writing sex with characters outside my OTPs is a new thing for me and I've done it twice now in the same story! Comment and let me know how I did :) Hope you enjoyed!


	8. Chapter 8

**Notes for the Chapter:**

> A minor non-con situation (groping without consent) appears in this chapter. It’s nothing huge, lasts for a few lines, and is dealt with, but figured I should put the warning out there. It wouldn't be there if it didn't serve the plot...what little plot there is.

Walking back to the Impala had been harder than Dean thought it would be. Every step down the two flights of stairs sent aching throbs through his body, his ass clenching with every movement, making it worse. Holy hell he was sore. There was a part of Dean that was satisfied by the pain, knowing how quickly his desire came back, this might hold off the need for a while. Another part though was uneasy, twitchy with the realization that if Gavin had had any intention of hurting him for real, Dean wouldn’t have been able to do anything to stop him. He’d been totally immobile in Gavin’s hold, trapped in the bigger man’s hands, between his arms, under his weight. Another man with a meaner streak could have really done some damage.

 

Dean rubbed a hand down the back of his neck, blowing a harsh breath through his lips. With everything he knows about the world, could he really put himself in a situation like that again? What if Gavin had been hurting him? What if he wouldn’t have stopped if Dean asked? What if Gavin hadn’t been a man at all, but a monster like the Winchesters hunted on a regular basis?

 

Dean licked his bottom lip and slid into Baby, running his hands over her dash to soothe himself. Even Aaron had put Dean into positions that confined his movements and was strong enough to keep him in place. Dean had no way of knowing that either Aaron or Gavin would treat him well, and he definitely had no way of knowing about anyone he got involved with in the future.

 

A turn of the key started Baby’s purr beneath him and he leaned back in the seat, letting her rumble gentle his nerves. He breathed deeply and put her in gear, turning the situation over and over in his head as he drove home.

 

***

 

The next few weeks carried the Winchesters to a new town with the end of Sam’s school year, a motel serving as their home until John decided it was time to move on again. Without Sam’s school to keep them in one place, their dad was even more willing to drag them around the country. John had departed on a hunt three days ago that he anticipated would last at least two weeks, so the boys were on their own and Dean was strangely relieved to be left alone with Sam. Though part of him was still uncomfortable in certain circumstances around his brother, it was much preferable to having Dad home and dealing with the paranoia that he would somehow find out about Dean’s preferences.

 

After arriving in the new town, Sam had reached out to a local youth group of sorts where he could spend some time during the long summer days and make some friends and Dean had found a part-time mechanics position at the local garage. They didn’t know for sure how long they’d be staying so they had to act as normally as possible in the meantime. It was low-key, simple, just how Dad preferred things so no one started asking questions. 

With Sam out of the house for long hours each day, Dean was able to snag a few moments for himself here and there to indulge his needs. Quick jerks in the shower each morning didn’t always cut it and those chances he got to go further were liberating and far more satisfying. Even still, Dean was starting to feel that itch under his skin again, that desperation to find a bed partner for the night, someone that would take him apart and fill him up. He shivered at the thought.

 

Wiping the back of his hand over his sweaty brow, Dean sighed and looked into the open hood of the red Toyota. An assessing nod and Dean was slamming the hood in place and cleaning up his tools before heading inside to the air-conditioned office. He grinned at Pete the owner sitting behind the desk and grabbed his time card. “Last one’s finished.”

 

The man returned the smile and lifted his hand in a wave. “Good to hear it. S’long as everything is cleaned up out there, you can head out.” In minutes, Dean was out the door and climbing into the stifling heat of the Impala. It was a Friday night and Dean had plans for pizza, beer, and whatever movie he could find on TV.

 

As he turned out of the parking lot Dean’s cell rang and he fumbled in his pocket before flipping it open and sliding it against his ear. “Dean.”

 

“It’s Sam. A few of the kids here invited me to a local pizza place and the movies tonight. I-uh, I want to go.”

 

Dean bit his lip but knew Sammy could handle himself. “Yeah? Good for you kiddo! Just keep me updated huh? So I know you’re good?”

 

“Yeah Dean, I will!” Dean could hear the smile in Sam’s voice.

 

“Have fun Sammy, but not too much fun if you get me.”

 

“I gotcha Dean. I will.” A long pause left only the sound of Sam’s breathing in Dean’s ear. “You’ll be okay? You don’t mind?

 

“Aw Sammy, you know me. I’ll be more than fine.”

 

“Yeah? Kay De’. Bye.”

 

“Bye bitch.” Dean heard a muffled “jerk” shout through the phone before he clicked it shut and tossed it on the seat beside him. He grinned. Little Sammy always trying to take care of his big brother. There was a part of Dean that missed the days when he made up Sam’s whole world, and vice versa, but he also knew it was healthy for Sam to have friends outside his brother. And this gave him the perfect chance to go out again if he could find somewhere local enough.

 

Now that Dean had different plans for the night, he needed to research a little bit and figure out where he could go. Noticing the sign for the local library, Dean turned in, fingers drumming on the steering wheel.

 

***

 

When Dean strolled out of the library, his cheeks slightly pink, the sky was turning a dusky purple. He rubbed a hand over the back of his neck and unlocked the Impala. Having been holed up in a musty corner of the library at the most discrete computer he could find, the fresh air was a welcome change. He inhaled deeply and dropped into his seat, sliding his hand over Baby’s dash. At least now he had somewhere to go.

 

Later that night after a heaping sandwich from the corner deli and a text from Sam saying he was still good, Dean set out for the bar he’d found during his search. This one was supposed to be a little less dance club, a little more regular bar with pool tables and dart boards, and Dean was hopeful that he’d feel a little more at home there.

 

Rather than hanging around nervously outside the bar, Dean pushed himself out of the Impala and through the front doors as soon as he parked. He rubbed sweaty palms on his jeans and settled in at the bar, exchanging his ID for a beer. Raising the bottle to his lips Dean glanced around, taking in the fairly low music playing in the background, the clank of balls crashing on the pool tables, the red haired woman wrapped around a shorter leggy brunette showing her how to throw a dart, and the two men a few stools over practically devouring each others’   
mouths. Dean felt color rise to his cheeks but managed to let himself relax into the scene.

 

Tipping the last sip back, Dean asked for another and wandered over to the pool tables, lingering by a table that had a game going. A few guys were gathered by the wall, watching another circle the table figuring out how to approach his next shot. They were older, maybe late twenties, but Dean knew that wouldn’t really matter. He watched for a few minutes, drumming up the nerve to approach someone himself. Both times before he’d been the one men came up to.

 

Still standing with his beer, Dean looked up and caught the eye of one of men, a smile curling across the guy’s mouth as he took in Dean’s face. A smile quirked Dean’s lips as well and he started towards the group. “Any of you up for a round?” he asked, nodding his head toward the table to their right, gaze intentionally remaining on the blue eyes of the man who’d caught his attention a few moments before, and fully aware of the double entendre.

 

“M’a take you up on that hot stuff.” Dean blinked and realized the words had slurred at him from the bearded guy standing two over from blue eyes.

 

“Man, shut up!” Blue eyes groaned, leaning out to glare at the man, to the great amusement of the other guys standing with them. “He doesn’t want your drunk ass fumbling around the table,” he paused and looked to Dean, “or fumbling over him.” He smirked and Dean blushed, dropping his eyes, raising his bottle to cover.

 

“F’ck off,” snarled Beard, brows pulled down in a glower. Dean really didn’t care about that and shrugged it off, again lifting his gaze to meet blue.

 

“I’m Dean,” he offered.

 

Blue eyes pushed himself off the wall. “Eric.” Dean soon found himself immersed in a game of pool with Eric and for once, wasn’t trying to hustle someone. He was playing a real game with a real guy who seemed to have a real interest in him. Dean fought back the giddy feeling fluttering around in his belly.

 

Dean was surprised to be enjoying himself so much, so he was slightly disappointed when it seemed like the game would end soon. As Dean was bent over the table with the cue stick, Eric came up behind him and pressed close, startling Dean so much he botched the shot, nervous laughter exploding from his lips. Standing up, he let his ass rub over Eric’s groin and he turned slightly to grin at the older man. Eric secured a hand to Dean’s hip and brushed a stubbled cheek against Dean’s.

 

“I really wanna take you home with me,” he murmured, lips brushing the shell of Dean’s ear. Dean’s eyes fluttered shut, a near-silent groan rumbling in his chest.

 

His throat bobbed and he nodded. “Yeah,” he breathed.

 

“How bout I grab us one more drink and we finish the game, huh?” Dean only nodded, his focus primarily on the heat soaking into his back. Then suddenly it was gone and Dean was left standing at the table alone.

 

The bar was more crowded by then, people waiting in tight masses for the bartender’s attention. It would take Eric a few minutes to come back so Dean refocused on the table, lining up different shots in his head, figuring out different ways he could play the table. It distracted him from waiting and helped stop the blood flow straight to his dick.

 

He was so focused that he jumped when an arm wrapped around his waist. “Back so soon?” he joked, twisting to see Eric’s face.

 

But it wasn’t Eric that greeted him. It was Beard, the sloshed guy from earlier. Frowning, Dean tried to push out of his hold, the hair rising on his arms when the man’s grasp didn’t budge. An arm came down on his other side to rest on the table ledge and then a hard bulge was being pressed against his ass. Dean squirmed. “Get off me man,” he growled.

 

“S’not like you don’ wannit,” slurred in his ear. “Been f’ckin askin f’r it all night. Bent over the table ‘n shit.”

 

“What the fuck man?” Dean could hear his voice rising in pitch but couldn’t do anything to stop it. “Get off.” The man’s hips ground against his ass again, a booted foot wedging between his own and kicking his feet apart.

 

Dean felt his instincts kick in. He snapped his elbow back and did his best to throw the guy back. With so little space, it didn’t do a whole lot, but it was enough that Beard took a step back. Dean was able to turn and feeling rage and shame bubbling in his stomach, threw his fist forward as hard as he could. It connected with the guy’s cheek and he went stumbling back into the table behind him.

 

By that point they’d drawn the crowd’s attention and Dean stared for a moment at the man who’d pushed himself on him and then turned, wide-eyed, to face everyone. Eric stepped forward cautiously. “Dean?”

 

Chest heaving, eyes flicking over the room, Dean turned on his heel and made a beeline for the door. Just as he pushed outside into the fresh air, a hand caught his wrist. He spun and pulled back, about to throw another punch when he saw Eric’s face. He shook out of the grasp on his arm and stepped backwards into the parking lot.

 

“Dean?” Eric tried again. “What’s going on? What happened?”

 

“Nothing,” Dean managed, voice shaky. “Nothing. I can’t do this.” He shook his head and backed up further.

 

Eric had taken a step forward, but stopped, putting his hands up in a placating gesture. There must have been something crazed about Dean’s eyes because he just said, “Okay. Okay. Are you alright?”

 

“Fine,” Dean spit out, and then he turned and speed-walked to his car, climbing inside and locking the doors. He braced his hands on the steering wheel and dropped his head back, staring at the ceiling and fighting back tears.

 

Fuck. He’d known. He’d fucking known something like this would happen, something that would show him how weak he was, how incapable he was of defending himself. Yeah, he’d gotten the guy off of him, even got away from him, but there was nothing to stop things like this from happening over and over again. He was young and even though he was pretty strong, he wasn’t very big. A guy with a mission, maybe a guy who was a little less wasted, and he wouldn’t have been able to shake him. He hadn’t been able to move out of Beard’s arms at first. Dean slammed a palm against the steering wheel and dropped his forehead against it.

 

After a few minutes of deep breathing, Dean sat up and turned the key in the ignition. Eric had already gone back inside and he needed to get away.

**Notes for the Chapter:**

> You know, I had this whole thing planned into the next chapter, but as I was writing I found myself wanting things to work out with Eric (at least as a one-night stand) even though I knew they wouldn’t. Funny how your writing and your characters surprise you sometimes…  
> Anyway, next chapter is in the works and should be posted soon! It was supposed to be part of this chapter but then it just kept getting longer and this felt like a good stopping point.


	9. Chapter 9

**Notes for the Chapter:**

> This chapter really could have gone with the last one, but I hadn’t finished editing yet, so here’s another short installment before a decently long and smutty chapter. Please enjoy!

Dean drove. He drove until his eyes blurred and his fingers turned numb around the steering wheel, but the blurring could have been from tears he refused to let fall. When he couldn’t stand it anymore Dean turned into the parking lot of a bar, a typical dive, and parked at the far side of the lot away from the other vehicles. Even feeling as he did, he wouldn’t jeopardize Baby.

 

Sniffing, Dean climbed out and strode inside, hands in his pockets, head ducked into his shoulders. He slid onto a stool, this time ordering a shot of whiskey and downing it in one. If whiskey could solve his dad’s problems, maybe it would serve him well tonight. The bartender refilled the glass and Dean sipped at it this time, feeling stupid and sorry for himself all at once.

 

Raising his head for the first time since coming inside, Dean glanced around at the other patrons. Dean didn’t think this was a college town, but it looked like a bunch of frat boys were gathered around a pool table in the corner, drinking, slapping each other’s shoulders, throwing sexual gestures and pantomimes each other’s way, laughing uproariously. There was a part of Dean that wished he had that life, had the chance to experience life so carefree.

 

In the opposite corner, wedged into a booth in the back was a middle-aged woman in a blouse, a glass in one hand, her other laid flat on the table. She seemed perfectly comfortable in the middle of a dive-bar, but also impatient, checking her watch every now and then and sighing as she sipped her cocktail. Dean imagined she was waiting on her lover or maybe just her husband after a long day at the office. A few tables down were a couple of older men, old friends it seemed, glasses half-full, table strewn with plates from a meal.

 

And gathered at the bar were clusters of friends, girls giggling over drinks and bent close to share secret tidbits about their lives, guys downing a few drinks together as a game was announced over the radio. Dean didn’t exactly fit in, but he didn’t not fit in either. There was nothing special about this place, nothing remarkable, and that was what made it safe. Dean’s shoulders dropped, losing some of the tension he’d built since running out of the last place. He took another sip and closed his eyes.

 

“Jack and club soda,” a voice husked over his left shoulder, a body sliding onto the stool next to him. Dean glanced, surprised to find a fairly young woman situating herself beside him. She was maybe twenty-four, brown hair, cut in choppy waves over her shoulders and fanned over her face, bangs swept off to the side, her body not “big” per se but not super thin either. She was striking in an understated way, not done up, but presentable, comfortable in her own skin, not trying too hard. Dean would have hit on her if he was still fooling himself into thinking women were his thing.

 

Dean looked away, sipped his drink. For a while he sat in silence, avoiding thoughts of before. For a little while he succeeded, but the problem surfaced where the thing you try not thinking about is of course the only thing you think about. His hand dropped to his leg, fingers picking at the seam of his jeans. He was growing restless and he hated it. The whole point of leaving there, of driving, of coming here was to avoid what happened earlier that night. Dean tipped back the rest of his drink, gesturing for a refill as soon as the glass hit the bar top.

 

“Wanna talk about it?” The woman on his left asked, the low rasp of her voice surprising despite having heard it before. She dropped one leg over the other and leaned in, her face honestly curious but not invasive.

 

Dean’s tongue dragged over his bottom lip. “No.” It was little more than a grunt. He caught her shrug out of the corner of his eye, sipping her drink casually, unaffected by her neighbor’s rude manners.

 

“Just seemed like there was something weighing on you. Thought maybe it would help if you talked to someone.” She wasn’t even looking at him, wasn’t thrusting her boobs in his face, wasn’t trying to flirt. It was kind of refreshing if Dean was honest, but he didn’t want to talk, not in the least. So why was he tempted to tell this girl about his night?

 

Dean swallowed and without so much as turning his head said, “Nothing to tell.”

 

This time she faced him and raised her eyebrow as if in disbelief, but turned back to her own glass. “Nothing, my ass. But whatever you want to tell yourself.” Dean glowered at his drink, swirling the contents. “So what’s got you around these parts? We don’t usually get too many new people around here.”

 

“You telling me nobody new ever comes through town?”

 

“Not that nobody does, just that people notice when they do.”

 

“So all these other people. You’re telling me that not one of them is unfamiliar?”

 

She glanced around, turning back with a smug smile. “Not a one. The woman in the corner? That’s Wendy. She and her son get together on a weekly basis. Tom and Gerry, yes those are their real names,” she smirked, “are old friends back from when they served together.” She pointed in the general direction of the other end of the bar. “All the girls are local, newly 21 for the most part, home from college on break. Most of the guys are the same or just never left.”

 

While she paused to sip her drink, Dean had a moment to take it all in. How amazing would it be to live in a town like this where everybody knew you? It wasn’t the first time Dean had thoughts like this, and he was never sure if he meant them, but there was something dream-like about not being on the move all the time, having a home base, people that cared or at least knew your name.

 

The girl resumed, gesturing over at the group of guys around the pool table. “The guys over there are a bunch of ego-inflated frat boys too self-involved to realize they’re not that funny. Also, home on break.” So Dean was right.

 

“And what about you?” Dean asked.

 

She smirked at him over the rim of her drink. “I’m Rhonda.”


	10. Chapter 10

Dean paused, wondering if there was a punch line in there, or something he was missing. The smirk caught him off guard and he wondered if somehow he’d asked the wrong question. He swallowed, decided not to let it bother him. She was a good distraction, no reason to end the conversation now.

 

“I’m Dean.” He waited a moment before continuing. “What, no backstory on you to finish out the introductions?”

 

She chuckled, a deep rasp that actually hit him under the collar just right. “Out of college two years now. Had plans to leave like the rest of the kids my age. Got pulled back after I graduated to take care of my mom.”

 

“You’re stuck in one place. I’m never in one place for very long,” Dean murmured under his breath. Rhonda remained quiet and Dean couldn’t tell if she’d heard him or not.

 

Just as he raised his glass, Rhonda asked, “So which one caught your fancy?”

 

Dean froze, turned slightly to face her. “What?”

 

She flicked a hand at the pool tables and repeated, “Which one caught your fancy?”

 

Dean choked on his most recent sip, raising a hand to cover his mouth. Grabbing the napkin being held in his face, Dean wiped his mouth. A flush rose to his cheeks, eyes darting to the bar top and staying there.

 

“So?” Swallowing thickly, Dean refused to lift his gaze, fingers biting into his knee and knuckles white around his glass. “Oh come on,” she dropped her voice, “You gonna try and tell me you weren’t just checking the guys out over there?” She waited and Dean saw her eyes roll. He clenched his jaw. “The whole time I’ve been talking to you, you haven’t once tried to hit on me, look down my shirt, or buy me a drink. You barely took half a second to look at the girls when I was talking about them…Aaand you’ve spent more time than you probably realize watching the guys down there and almost drooled when I pointed over at the pool table.”

 

Dean would be lucky if he walked out of here breathing tonight. His chest felt so tight he couldn’t tell if he was pulling in air. Lifting up slightly from his seat, Dean pulled out his wallet and fumbled out a few bills, shoving it back in his pocket as he slid off his stool.

 

Before he could take a step, Rhonda put a gentle but firm hand on his wrist. “I’ve been told on multiple occasions that I have a habit of over-stepping. They’re probably right, but well, it’s gotten me this far.” She shrugged. “Look, I don’t know what exactly your situation is, and honestly it’s not my business, but would you like to come home with me?”

 

Again, Dean froze. “What?” He couldn’t wrap his head around that one. She’d seen – she’d literally pointed out his interest in men. He stared at her.

 

Rhonda licked her bottom lip and met his eyes, leaning in close so he could hear her whisper. “You have a thing for cock. I just happen to be a bit kinky. I’m thinking we can work something out.”

 

Dean choked on his next breath. Who the fuck just came out and said stuff like that? He was surprised, but part of him was turned on, the part that must have reacted to her voice earlier in the night.

 

With the situation from earlier that evening, Dean knew hooking up with men wasn’t exactly the safest thing he could do. He’d been lucky with both Aaron and Gavin, but Beard had proven to him that his fears were founded in real possibility and Dean couldn’t risk being stuck in a position where he couldn’t get out. This might be a good way of figuring out what _was_ possible. It wasn’t what he expected out of this night, but there was still a desperation pumping through his veins, a need to be with someone, to be filled. And it sounded like maybe Rhonda could do that for him.

 

Why the hell not? Dean met her eyes. “Okay,” he breathed.

 

***

 

At her apartment, Dean perched on the edge of the couch, sweaty palms pressed to his knees. Rhonda was in the kitchen getting them drinks, an effort to ease them both into what would come next, but Dean wasn’t sure anything would help, not with this. He peered around the room, eyes flicking from the crochet blanket bunched on the other end of the couch to the blank TV, to the stack of magazines on the coffee table, to the heap of movie tapes knocked over on the floor.

 

“Trying to find my super secret stash of kinky porn?”

 

Dean froze and looked up at Rhonda where she leaned in the kitchen doorway. “Wh-what? No.” Dean wasn’t sure his answer was convincing. He was a bit taken aback by her forwardness and how uncomfortable he was around her. He was usually so smooth around women that it was discomfiting how much he _didn’t_ have figured out about this one.

 

“Relax Dean,” she laughed, coming out to sit with him on the couch, handing him a beer and curling up with hers against the pillows. “I’m kidding hon.” She patted his leg. “You sure you wanna do this?”

 

There were words, words he should be saying, but Dean was again stuck in place, unsure how to proceed.

 

“How ‘bout this. I tell you some ideas I have for how tonight could go and you nod yes or no.” She raised an eyebrow at him, an encouraging smile gracing her face.

 

Breathing deeply, Dean nodded and allowed himself to be pushed back into the cushions. Rhonda gave him an assessing look. “Before I say anything else, I need to know your preference. Are you a top?” Dean inhaled but didn’t move, couldn’t. “Bottom?” She prompted.

 

Blushing, Dean gave a short nod. So much for all that confidence Aaron encouraged him to have. He was back to blushing and not meeting people’s eyes like nothing had changed.

 

“Interesting,” Rhonda remarked, trailing a finger down his leg. “Nothing to be embarrassed about. I find it…very hot.” Dean’s cheeks flamed. She smirked, “Let’s get to it then. Feelings on a hand-job.” Dean nodded.

 

“Blow-job.” Another nod. “Fingering.” Dean swallowed thickly, but lowered his chin in a nod.

 

“Toys.” Dean paused, staring at her considering. “Like a dildo or a vibrator.” Dean lifted his chin this time, another yes. He was baffled by how straightforward she was about all this, how unashamed.

 

“Pegging,” she offered, this time with a brow raised. Teeth sank into Dean’s bottom lip, his mouth suddenly dry. “As in I would –” She was cut off by Dean’s nod and grinned. “So you do know what that is. Good. Bondage.”

 

Immediately, Dean shook his head, on guard. Rhonda raised her free hand. “Just a suggestion hon. No biggie. Spanking.” Another shake.

 

She nodded in understanding. “Can I touch your nipples?” Dean couldn’t help the laugh that escaped, but he nodded, settling back more easily into the couch.

 

Rhonda sipped her drink, watching him. She wet her lips. “Panties.” Again unsure, Dean froze, eyes flicking up to hers and remaining there, trying to figure out if she was joking with him or making fun somehow. He started to shake his head, then stopped, cocking his head at her. A smile answered him. “I think you’d look fucking hot…and what’s this night for if not a little experimentation. You up for it?”

 

Tongue darting out to wet his lips, Dean looked away, thinking. He was suddenly desperately curious and despite his misgivings, he nodded.

 

“Wonderful. You want to finish that drink or jump right in?”

 

Dean looked at the bottle sweating in his hand in surprise. So absorbed by Rhonda’s suggestions and his discomfort, he’d barely managed to take more than two sips. He tipped it back and sucked down a few deep swallows before setting it on the coffee table and standing. “Let’s go,” he managed to rasp out, extending a hand to Rhonda on the couch.

 

She husked a laugh and allowed him to guide her up, then pulled him along to her bedroom.

 

***

 

Inside the room, Dean was surprised to find a mixture of furniture and decorations that didn’t scream mature super confidant intimidating woman like he expected. He’d half expected her room to be a combination of deep reds, blacks, and leather, but what the fuck did he know. Instead her room was painted a light green, gauzy sequined curtains draped over the windows. Her bed cover was cream-colored, plush and far more innocent than he’d imagined with a stuffed rabbit leaning against the pillows. A glance around showed him a dresser, the top drawer hanging open with fabric spilling out, a small pile of clothes pooled in front of the closet.

 

Dean inhaled deeply, her humanness calming him, allowing him to relax somewhat. Something about seeing her space put him at ease. She seemed to sense the tension leaving him and tugged him further into the room, pushing down on his shoulders so he was seated on the end of her bed.

 

With him seated Rhonda stepped back and walked around him, bending to open a large drawer built into the frame of her bed. Dean turned to watch and his jaw dropped instantly at the sight of so many panties. “You want to take a look?” Rhonda asked, peering up at him from where she was crouched.

 

Dean simply nodded, wide-eyed. Rhonda dropped into a cross-legged position and patted the spot next to her. Feeling awkward, Dean slid to the floor and sat next to her putting his hands in his lap. “Here silly, go through them, see if any catch your attention.”

 

There were so many Dean was overwhelmed – lace and satin and silk, mixes of different fabrics, bows, scalloped edges, bikini cuts, briefs, boy shorts, assless, crotchless, and ones with straps going places he didn’t understand. The red in his cheeks was starting to feel like a health-hazard. Was it possible for so much blood to be in his face and for the rest of his body to still function?

 

Rhonda was gliding her hands through the piles alongside him, assessing and discarding as she went. Dean didn’t know where to begin. He pulled back and laid his hands on his knees. Noticing how Dean retreated, Rhonda turned to him and smiled. “Maybe I should pick?”

 

Dean met her eyes. “Please do,” he managed, “I’ve got no…” he fumbled over the words, raising his hands to show his confusion. “There’s so many.”

 

Rhonda laughed, her eyes lighting up with humor. “Sure are, and oh the memories attached to some of them! How ‘bout you take your clothes off and I’ll find a good pair for you.” She shooed him away.

 

Amazingly Dean felt some of the tension ease again, and climbed to his feet. As he shucked his clothes, he couldn’t help glancing over and breathed a sigh of relief when he saw a strappy pair fall in the discard pile.

 

As soon as he was down to his boxers, Rhonda announced, “Got ‘em. These’ll look perfect on you.”   Dean turned to find satiny pink panties with black lace sides dangling over her finger.

 

“Pink?” Dean asked, disbelieving.

 

Rhonda smirked. “Your cheeks inspired me, hon. Pink looks good on you.”

 

As if to compliment her words, Dean’s cheeks lit up once more, heat spreading over his face and down over his chest. Snatching the panties from her hand, Dean dropped his boxers around his feet and stepped into them, amazed to find that the fabric felt fucking awesome gliding over his skin. He drew the waistband up and had to maneuver a bit before he settled his cock into a somewhat comfortable position. He was squished and was convinced he looked ridiculous, but they were on.

 

Standing by her closet, Rhonda crooked a finger at him, a knowing grin on her face, and going over to stand by her, Dean was spun to face a mirror. He sucked in a breath. Part of him was still scoffing at the idea of him in panties, but the part at the forefront right now was preening, amazed at how good he actually looked in them and how comfortable they were starting to become. A black bow adorned the front as if decorating his cock and even that was strangely enticing. “Fuck me,” he murmured, staring at himself.

 

From behind him, Rhonda chuckled. “Plan to.” Dean rubbed a hand over the back of his neck. She laughed again and patted his ass. “Keep admiring yourself. I’m going to get a few things ready.”

 

He heard things shuffling and moving around for a minute and then she was gone. For a few minutes Dean was alone, just him and his reflection. Damn, he looked surprisingly good and definitely not as stupid as he’d feared. His curiosity had been worth it – these looked and felt amazing. He turned to see his ass. His cheeks peeked out of the bottom, the material cut more narrowly just for that effect.

 

He’d fuck him.

 

The more he stared, the more enamored he became. His cock twitched and Dean groaned, the feeling of the fabric pressing back on him strangely arousing. He reached a hand down, cupped himself, and moaned at how sensitive he felt through the material. He was getting harder and licked his lips when he saw the wet spot blossoming around the head.

 

A clatter sounded in the apartment and Dean remembered he wasn’t alone. “You coming back?” He called, suddenly feeling stronger and more confident than he had all evening.

 

“Just a sec!”

 

As he waited, Dean wandered back over to the bed and sat down, leaning back on a hand. The other settled on his thigh and watching his own lap, Dean trailed his fingertips over his leg, over his belly and up his chest. He pinched a nipple and groaned, cock twitching in the panties, wet spot spreading.

 

“Fuck,” he heard whispered from the doorway. He glanced up lazily, eyes hooded, and grinned crookedly at her.

 

“Like what you see?” The words came out in a husk, arousal clouding his vocal chords.

 

“Oh yeah. Goddamn, you look fucking stunning.” Rhonda was looking at him with pure lust in her eyes and even though it was a woman, Dean could feel himself responding, felt the arousal heating his blood, making the desperation from earlier come back stronger. She went over to the nightstand and organized whatever she’d brought into the room before coming back and just standing in front of him.

 

After a moment of admiring him, Rhonda dropped to her knees and situated herself between Dean’s legs. She trailed her fingers from his knees up to the crease between his groin and thigh, grinning at the hiss that escaped Dean’s lips. She feathered her fingers over his skin and as one hand braced on the inside of his thigh, the other curled around his cock, pressing the smooth fabric into his skin, sending his head rocking back.

 

The soft pressure was making Dean crazy and the lighter she touched, the more Dean tried to rock his hips forward, desperate for more contact, for harder. Rhonda teased him for endless minutes, drawing back each time Dean sought out more of her touch and pressing harder each time he settled. She laughed throatily, Dean’s cheeks reddening even as he again rocked his hips into her palm.

 

Teeth bit into his bottom lip. And then finally, finally, wet heat was on his cock, Rhonda’s mouth sucking in gentle motions over him through the panties. She lapped at the sodden spot in the fabric, teasing him in elongated strokes that both gave him the sensations he needed and denied him the full pleasure of it. As she sucked at the head, her hand moved to cup his balls, rolling them in her palm and triggering another roll of his hips. Dean breathed a moan, amazed by how satisfying this strange experience was becoming.

 

Hands soothing back down Dean’s thighs, Rhonda sucked harder at Dean’s tip through the material. Dean’s back arched, a soft sound emitting from his throat, a cross between a whine and a whimper. And then Dean was in motion, his hips jerked roughly to the edge of the bed, his ass situated just this side of falling off.

 

An embarrassing squeak left his lips and Dean felt the blood rush to his cheeks even as more rushed to his cock making it twitch within its confines. Before Dean could voice his – discomfort? surprise? Dean didn’t quite know what he was feeling in the moment – Rhonda had followed the first motion with another, tipping him back and pressing his legs wider.

 

He was still wearing the panties, but he’d never felt so vulnerable while still wearing any sort of clothing – flat on his back, legs bent into his chest, ass in the face of the woman between his legs, Dean was feeling very vulnerable. Not knowing what else to do besides accept whatever Rhonda decided to do with him, Dean closed his eyes and curled his fingers into the fabric of her comforter.

 

Rhonda dipped back down, sucking softly at his cock through the fabric, tongue tracing in wet circles around the head of his cock and down to the base. She again massaged at his balls through the panties and then she was soothing his legs back down to drop limply over the edge of the bed. She feathered her fingers over Dean’s stomach, her mouth still sending bliss through his body until she pulled away and fingered the waistband of the panties, lifting them up and over his cock to settle them below his balls.

 

The feeling wasn’t exactly comfortable, the fabric pulled taut where it was pulled tight against the swell of his ass and now down below where it was supposed to be, but it was still strangely sexy. Dean felt debauched and it was exhilarating. His fingers flexed in the covers.

 

“I’m gonna suck your cock now,” Rhonda’s voice husked from between his legs, her hands again pushing his thighs up, situating his heels on the edge of the mattress. He groaned and lost his breath as in one fluid motion she sucked him down.

 

Between one second and the next, Dean was engulfed in hot wet rapture. What pleasure he was experiencing through the panties, was now magnified, his cock now encased by her mouth, squeezed tight by her throat. He gasped and bit back a shout. Her teeth had just barely grazed him as she’d pulled back, but that too was amazing and Dean felt any and all embarrassment or reservations he’d still had about this night disappear.

 

He’d had blowjobs before, been with women before. He’d even enjoyed women before, but since realizing his desire for men, that enjoyment had paled and lost its appeal. Dean had been highly skeptical about going home with Rhonda, even more so when she asked him to put on her panties, but it was perhaps because, no it was definitely because of the panties, because his boundaries were being pushed, that this was turning into an awesome experience, one of the best of his life.

 

Dean groaned as Rhonda again sucked him all the way into her throat, swallowing around him. It had been so long since he’d felt this good. The whole reason he’d gone out tonight was because he’d so desperately needed to feel this way. A woman between his legs or not, Dean was feeling fucking amazing.

 

As Rhonda sucked him down and bobbed over his cock, her hands rubbed at his thighs, soothing over his skin and adding to the sensations. Goosebumps rose on his skin and then Dean was jerking his hips up, startled when a hand trailed onto his ass and then between his cheeks, massaging at his hole through the silky fabric. One finger pressing firmly against the furled muscle, Dean choked back a whimper, suddenly desperate for more. God, he needed more. Fuck. His hips jerked again and Dean was lucky Rhonda was so into this or he might have an angry chick on his hands for nearly choking her.

 

With Dean still in her mouth, Rhonda pressed more firmly, the tip of her finger just breaching Dean’s hole. “Oh fuck,” he gasped.

 

She pulled off and smirked at him. “Good, huh?”

 

Dean swallowed thickly and nodded. “Please,” he whispered.

 

“Mm, you got it hon.” Rhonda patted Dean’s hip and stood, going to the side table and coming back with a tube of lube. She waved it next to her face and grinned. “Let’s make this as smooth as possible, huh?”

 

Dean blushed and closed his eyes, grateful when Rhonda simply knelt back down and didn’t say anything else. He heard the click of the lid opening and then a wet squelch. He licked his lips nervously, jumping when he felt her fingers worm their way under the panties and smear over his hole. Without pressing in, Rhonda pulled her hand back and returned to the outside of the fabric.

 

Cock bobbing against his stomach, Dean was eager to continue, but again, he was feeling a bit nervous. Rhonda rubbed at Dean’s hole again through the panties, leaning in to lap at his balls. She pushed a fingertip inside. Dean sucked in a breath. “Won’t that ruin them,” Dean managed around another gasp.

 

Rhonda responded with her lips grazing his cock. “Don’t you worry about that. Just focus on how good this feels.” All Dean could do was nod, hips rocking into the different sensations. “You should see how amazing you look,” she whispered, almost not talking to him.

 

Rhonda pushed in deeper, his ass sucking her finger and the panties inside without a fight. “Oh god, oh god, fuck!” Dean bit his lips and imagined what it must look like as Rhonda’s finger disappeared completely inside him, panties puckered around the digit and just as deep in his body. The lube eased the way and without warning, Rhonda pulled out and pushed in again, this time with two fingers. She fingered him until he was breathless and gasping for air, and then kept going, whispering how hot and amazing he was under her breath.

 

Dean couldn't breathe, his lungs fighting to take in air as his ass clenched around her two fingers. For a brief moment, Rhonda paused and then again she continued, but with three fingers instead of two. A choked cry left his lips and Dean lifted his hips to meet her fingers, rocking against the strokes of her hand, desperate for more, to feel her deeper. “Please,” he whispered through bite-swollen lips. “Please.”

 

“I gotcha, Dean,” Rhonda soothed, fingering him just a little longer before pulling her fingers out. Staring at the ceiling, Dean waited, anxious to continue. And then there was something else pressing at his hole, something more solid and rounded than Rhonda’s fingers, not so warm.

 

“W-what–” Dean tried to ask.

 

Lifting it so he could see, Rhonda answered. “It’s just a vibe Dean. You still okay with that?” Licking suddenly dry lips, Dean nodded.

 

Smiling, Rhonda moved the vibe back against his hole and gave it a little pressure. Dean’s breath caught in his throat as just the tip slid inside, pushing the panties back into his lube slick hole along with it. As Rhonda pressed it deeper, filling him up, Dean’s back arched off the mattress and his fingers clenched tighter in the comforter, curling fabric around his hands.

 

“You’re so hot Dean, doing so well with all this,” Rhonda encouraged. Dean’s head dropped to the side, unsure but really wanting to believe her.

 

Then with the vibe situated deep inside, panties still pressed deep, Dean felt it rip to life, vibrations rushing through his body all at once. Dean sobbed, tossing his head, his whole body tensing at how completely engulfing it was. He briefly recalled the intense feeling of the electric toothbrush Sam had retrieved for him, but this – so deep inside, so strong – this was so much more.

 

Rhonda stroked a hand over Dean’s thigh and over his hip, holding him in place as she began fucking him with the vibrator. It wasn’t exactly thick or even all that long, but after all the buildup Dean was feeling extremely sensitive and like he could come from just this. He moaned and held back a cry as finally, fucking finally, the little device hit his prostate.

 

His hips shot off the bed, rocking hard into Rhonda’s hand. Dean tried to muffle his shout as Rhonda drove it inside again. Fuck, this was amazing. For endless minutes, Rhonda fucked Dean with the toy, twisting it and angling at different times to add to his pleasure, surprising him into cries of delight when the vibrations hit just the right spot.

 

“P-please,” Dean murmured, head tossing to the side. Eyes rolling back, he couldn’t stop the words from spilling out. “God, Rhonda please. I need more.”

 

Rhonda pounded the toy in harder for a few strokes. “Can’t take anymore Dean? Does your hole need a big fat cock?” Dean felt his cheeks flare red in embarrassment. He refused to meet Rhonda’s eyes even as he lifted his hips to meet her hand. “I’ve gotcha Dean, don’t worry. I’ll fill you up real soon.”

 

Dean huffed a breath, panting as Rhonda’s pace continued unhindered. His chest was tight, stuck between inhaling and having the air punched out of him on repeat. “Pl-ease,” he moaned with what little breath he could manage.

 

Rhonda smirked and finally, finally switched the vibe off. Dean gasped for air, his thighs trembling as Rhonda slipped the toy free. The lube-soaked panties pulled free as well and Dean made a face at the uncomfortable feeling.

 

Chest heaving, Dean peered down the length of his body at Rhonda who grinned wickedly. She patted the outside of his thigh as she dropped the toy to the floor. Surprising Dean, she dipped her fingers under the waistband of the panties and tugged, urging him to lift his hips as she pulled down and guided the now soaked and stretched fabric over his still hard cock and free of his legs.

 

“Scoot up,” she said, her eyes dark. Dean swallowed hard and did as she asked, sliding his body backwards until he met the mound of pillows settled against the headboard, dick bobbing with the motion. Feeling an uncomfortable shape at his back, Dean reached behind him and pulled out the stuffed rabbit he’d first noticed when entering the room. Snorting a laugh, Dean perched it on the nightstand, hearing Rhonda chuckle as he angled its face away from the bed. Adjusting so he was leaning comfortably, Dean watched as Rhonda followed him up the mattress and knelt between his legs.

“Comfy?” Rhonda asked, raising an eyebrow.

 

Feeling a tad bit more confident than earlier in the evening, Dean snorted again and nodded, resting a hand low on his belly, thumb and pointer framing his cock, legs splayed around Rhonda between them. “Wonderful,” she leered, settling her hands at the tops of Dean’s thighs, her thumbs gently stroking the crease between leg and hip. “Stay just like this,” she guided, easing his shoulders further back and adjusting his legs so his hips were settled a little further down the mattress. She feathered her fingers over his chest, grazing over his nipples and then his cock before reaching for the lube.

 

A slurping suction sound echoed in the room and Dean flinched, again trying to ignore the fact that there was a woman rather than the desired man about to fuck him. He breathed deeply, watching Rhonda through barely opened eyes. Gel on her fingertips, Rhonda watched his face as her hand neared his ass, biting her lip against a grin as cold met heat-warmed skin. Dean hissed and glared mildly at Rhonda, shifting his hips in a pointless attempt to escape the cold.

 

Still open from the vibrator, Rhonda was able to press right in with one finger, curling the digit and then pulling back to add another. The near immediate increase in size forced a groan from Dean’s throat, but the width and pressure felt good and god, it didn’t even matter that the fingers belonged to a woman. They moved with practiced ease and in seconds were pressing just right on the sweet spot inside, Dean’s shoulders pressing deeper into the pillows as his hips fought to lift into her hand.

 

With a few more presses and tickling massages over his prostate, Rhonda added another finger, the three now scissoring apart and twisting and curling to send lightning strikes through him. Dean’s mouth was dropped in bliss, unable to contain the quiet mewls of pleasure as she continued to hit all the right places in just the right way. It was truly remarkable how good she was at playing his body.

 

Dean’s hips rolled into her hand and he groaned, desperately needing to come. Rhonda hadn’t pushed him that far yet, holding back just enough that he hadn’t fallen over the edge, but he could feel the need growing.

 

Dean’s hands gripped the comforter, fighting back a surprised groan as Rhonda pressed in a fourth finger. “Holy fuck,” Dean bit out, his chest tight with the inability to pull in full breaths. She pumped her hand in quick short motions, spreading her fingers with each thrust inside, flexing them to drag over his sweet spot. A twist of all four fingers sent another bolt of pleasure through his spine and Dean couldn’t hold back a whimper. His hips rocked down into her hand in a desperate bid to get her deeper inside.

 

Seeming to know what he wanted, Rhonda retreated each time he pushed down against her, again keeping him just this side of coming. Even still, Dean could feel the heat building in his lower stomach, felt his abs tensing, jaw dropping as the pleasure built, and then a tight grip wrapped around the base of his cock, a thumb pressed rigidly against the underside.

An embarrassing sobbing sound escaped Dean’s throat, his knuckles white where they curled deathly tight in the fabric beneath him. “Not yet Dean,” Rhonda whispered, her voice a low rasp in the otherwise quiet room.

 

“I-I need,” Dean shook his head on the pillow, tears pricking the backs of his eyes he so desperately needed to come.

 

“I know. You still okay with all this?” Dean gave a wide-eyed nod, floored that she was even asking. Wasn’t it damn fucking obvious? “I need to hear you say it. It’s important Dean.”

 

Dean wet his lips. “Yes, I’m okay with this. Now fucking get on with it.”

 

“You’ve got quite the mouth,” Rhonda smirked, leaning back on her knees. “One last question. Do you mind if I take my clothes off?”

 

Dean froze, thoughts jarring and suddenly feeling really bad and unsure about how he’d come across to her. “Of course not! I’m just – you’re just – I,” Dean stumbled. “You’re a beautiful woman, I just um I just, you know, like the male body more.” By the time he got the final word out, it was a whisper and Dean’s face was bright red, the tips of his ears pink.

 

Rhonda chuckled. “I’m not fishing for compliments hon. I just want you to be comfortable.”

 

Still bright red, Dean managed, “It’s fine.”

 

Nodding, Rhonda stood from the bed and undressed, a casual unveiling that was neither clinical nor sexual. Dean liked that this woman was herself no matter what, that she didn’t put on masks or do anything to change herself. He could appreciate that, even noted that she was beautiful, curvy in all the right places on a woman and confident in her skin.

 

As Dean watched, she piled her clothes on the floor and stepped over to the nightstand where she’d earlier placed a few of her supplies. Rhonda picked up the strap-on from the tabletop, Dean’s eyes growing wide at the sight. He pushed himself into a seated position, tense against the pillows. Dean hadn’t paid Rhonda’s supplies any mind until now and though he was still achingly hard, he was suddenly unsure now that he’d seen the toy.

 

The strap-on was a deep purple, long and realistically ridged with a mushroomed tip on either end. Yeah, he’d fucked himself on his self-made toys before, even been with two male partners by this point, but there was something about being faced with this toy that had him out of sorts.

 

Rhonda smiled at him, coming to sit on the edge of the bed, resting the toy in her lap. She placed a hand on Dean’s thigh, rubbing her thumb over the skin just above his knee. “Dean, hon, it’s okay. I know it looks a bit intimidating,” she said, lifting the toy and giving it a little shake, “but I promise you it’s not that bad.” Dean smiled nervously, only one side of his mouth lifting.

 

Rhonda leaned in and gave him a crooked smile. “You’ve had cock before Dean. You loved what we were doing earlier. This won’t be so different from those things. And Dean,” she brought the toy closer to him for him to see better, “remember that one end of this is for me. There’s only half of this for you to take. I’ll take care of you.”

 

Dean stared at the toy she held in front of him and breathed shakily. Swallowing thickly, he gave a short nod. “Okay.”

 

Rhonda grinned and stood again. “Good. Okay, well I’m going to get this situated, so why don’t you give yourself some love while I do that.”

 

Dean blushed bright red again, eyes darting away from her. In his worry and the sudden tension, his erection had waned some, so Dean did what Rhonda said, stroking himself back to full hardness. Unsure if he really wanted to watch or not, Dean shot side-ways glances at Rhonda, watching her as she got herself ready with the toy.

 

She stepped into the straps until they were just under her hips and then with a little squat to part her legs, lifted one end of the dildo between her lips. Dean swallowed and licked his bottom lip, shifting his eyes away and back again, curious.

 

Rhonda dropped her head back as she eased the toy inside, groaning softly as it filled her. Adjusting the straps to sit around her waist, Rhonda looked to Dean. “I know this is all a little weird for you. It might be easier if you can’t see me when we do this.” She climbed back onto the bed, bracing her knees apart on the mattress, purple dick protruding from her groin and looking strange but also enticing.

 

Dean was suddenly very into this all over again, his need to be filled from earlier in the night returning full force. His hole throbbed and his hips rocked up into his hand. “Fuck,” he whispered.

 

“Go ahead Dean, up on your hands and knees.” Dean scrambled up, turning his back to her, settling his palms into the mattress and dropping his head down between his shoulders. Rhonda moved up between his legs and reached out, soothing a hand over his lower back, the other pulling one cheek to the side. She thumbed over his hole and seeming satisfied, pulled her hand away.

 

A snick echoed in the room and Dean knew that Rhonda was opening the lube again. A finger slicked over his hole and pressed gently inside, easing the way. When Rhonda pulled away again, Dean could hear a slick sliding sound and trembled, recognizing the sound of lube being applied to cock.

 

Rhonda lightly gripped Dean’s hip and with the other hand, positioned the dildo at Dean’s entrance. She rubbed the cool tip over his hole. Dean let out a breathy moan, his arms already feeling weaker knowing what was to come. He held his breath, equal parts anxious and excited.

 

Without further warning, Rhonda shifted her hips forward and the thick plastic cockhead eased its way inside. Dean’s breath hissed out of his lungs at the pressure and instant fullness. “Okay?” Rhonda asked, her thumb again rubbing in circles where it rested at the back of his hip.

 

“Y-yeah,” Dean managed, holding perfectly still. At Dean’s answer Rhonda continued to press forward, sinking deeper inside at a steady pace. In no time at all the cock was balls deep in his ass and Dean’s eyes fluttered closed at the sensation. Finally. Goddamn finally.

 

Gently, Rhonda pulled back in small increments before rocking in again. Dean’s breath caught at each thrust forward, the thick fullness beginning to settle the need he’d felt all night. As he grew more accustomed to the movement and feel of the dildo inside him, Dean began slowly rocking his hips back to meet Rhonda’s motions.

 

One particular thrust backwards of his hips forced a pleasured groan from her mouth. “That’s it Dean. Just like that.”

 

They rocked in sync for a short time and then Rhonda surprised him by surging her hips forward and grinding against him. Dean threw his head back on a loud moan. She did it again, and again, and Dean’s eyes rolled back as a new angle forced the head of the dildo to graze over his prostate.

 

Arms too weak to hold him up, Dean dropped to his elbows, his ass lifting higher in the air, again changing the angle. The dildo was now perfectly hitting his prostate every time and it was driving him fucking crazy. He turned his face into the crook of one arm, a sobbed moan muffled into his skin. A breathy punched out “ah” escaped his lips, quickly followed by another with each surge inside, Rhonda’s hips now slamming forward on each thrust, her hands clenched tightly around his hips.

 

Sweat dripped from Dean’s hairline and formed a sheen over his back. He felt Rhonda’s hands slip over his skin and it somehow only made everything better. He was drowning in pleasure and the feeling of finally being full, so full.

 

His own toys had stopped cutting it a while ago and it had been so long since he was with someone he thought he’d combust. He’d started to lose hope that he’d get what he needed again, so nervous about being overpowered after how Gavin had been able to manhandle him, how the man from earlier that night had held him immobile.

 

There wasn’t a man behind him, and there wasn’t a hot throbbing cock inside him, but he _was_ getting fucked and there _was_ the force of someone’s hips behind it. This was far more satisfying than anything he could do to himself.

 

He whimpered as Rhonda twisted her hips, the drag against his sensitive walls and his prostate sending his pleasure center into overdrive. He didn’t know how much more he could take before he fell over the edge. He’d been dangling over it for so long, there wasn’t much left of his grip.

 

“I’m so close,” Dean whimpered, the words little more than a whisper. His body rocked with the force of Rhonda’s thrusts, back arching, hips rolling, pressing him closer to the cock inside him. It was incredible – long, thick, full.

 

Face still tucked into his arm, Dean tried to stifle a whine, fingers curling into the comforter. Rhonda was purposely driving her hips forward at the same angle, the dildo brushing his prostate. His skin was flushed hot with pleasure, his skin too warm and beginning to feel oversensitive, prickling and tingling, almost too much for him to handle.

 

Behind him soft moans spilled from Rhonda. Dean did his best to meet her thrusts, give the pleasure back to her, but from his position, there was only so much he could do. She had the control and fuck, she knew what to do with it.

 

Rhonda leaned forward, fingers pressed hard into his skin, her hips picking up speed. “Touch yourself hon.”

 

Dean whimpered again into his arm, the new angle even better than the last. Frantic with need, he followed Rhonda’s directions, sliding one hand from its hold on the covers to his cock. He pressed his palm against his length, massaging it against his stomach for a moment before wrapping his fingers around it and giving a tug. Slick with pre-come, Dean’s hand slid easily over his cock. He was amazed by how wet he’d gotten, even more surprised by how hot he found it. He rocked back against Rhonda and continued jerking his cock, his hand keeping time with her hips.

 

“So good,” he mewled into the comforter, the bubbling heat in his belly about to boil over. Feeling a tingle start low in his spine, Dean slid his hand faster. Rhonda’s hips were losing their rhythm and then he felt her shudder over his back, a whimpered groan sounding behind him. Knowing she had let go, Dean allowed himself to fall over the edge, a cry muffled into his arm, vision whiting out.

 

Dean’s hand flew over his cock as his body shook, all of the desire, sensation, and pleasure of the night convalescing into a storm ravaging his body. His hips rolled, continuing to rock him between his palm and the dildo still inside him.

 

His hand slowed, breaths coming fast, still trembling. He couldn’t move, feared that if he did, his body would just shake apart. Behind him he felt Rhonda remove herself from where she had leaned over his back, grazing a hand over his spine as she withdrew her hips, the dildo sliding free of him with one last squelch.

 

Dean’s body shook harder at the sensation, feeling so good but also so suddenly empty. He let himself sink down into the mattress, boneless. “Fuck,” he breathed.

 

Rhonda laughed behind him, the bed shifting under her movement. “Mmm,” she seemed to agree with him, “Feelin’ pretty good huh?”

 

Dean could do little more than chuckle back. He was floating. Rhonda let him lay there for a while and then Dean started to notice the drying mess under his belly. He pushed himself onto his knees, brushing a hand over his abdomen. “Shit, sorry ‘bout the mess.” His cheeks heated.

 

Rhonda waved a hand at him. “Don’t worry about it. You more than made up for it.” She gave him a leer. Red rushed to his cheeks again and he ducked away from her gaze.

 

“Can I help you clean up at all?” Dean climbed off the bed and stood awkwardly next to it. Now that the sex was over, he wasn’t exactly sure what to do. This somehow felt different from being at Aaron’s or Gavin’s.

 

“Nah, I got it,” Rhonda assured him, tugging the comforter from her bed and rolling it into a ball. “The bathroom’s across the hall though if you want to clean yourself up. I’m gonna go put this in the wash.”

 

“Yeah, I’ll do that.” Dean searched the room briefly for his clothes and went to clean up. When he returned, feeling much better without come smeared over his stomach and lube leaking out of his ass, he pulled his clothes back on.

 

Glancing around the room for any missing items, Dean’s eye caught the small pile of pink just to the side of the bed. Checking to see if Rhonda was coming, Dean bent to pick the panties up. They were still damp, but Dean stuffed them into his pocket anyway. As stupid as it was, Dean couldn’t resist having the souvenir.

 

He exited the room and wandered until he found Rhonda. She was just coming out of the laundry room, still naked, seeming completely comfortable. Dean really liked that about her. “I’ve gotta head out, um, gotta get back to my brother.”

 

Rhonda met his gaze, a half smile quirking her mouth. “It was an absolute pleasure to meet you Dean.” It was almost a purr and Dean felt his cheeks turning red once more.

 

He dropped his gaze to the floor. “You too,” Dean replied, “and uh-thank you.” He rubbed a hand over the back of his neck.

 

Rhonda stepped closer, tipping his chin up. “You’re more than welcome, hon. I really hope you find what you’re looking for, Dean.” Dean closed his eyes, swallowing thickly.

 

“Yeah, me too.” Rhonda pulled him into a hug and with a kiss on the cheek, released him, giving his ass a pat as she directed him towards her front door. Dean burst into startled laughter and stepped outside, walking in a slight daze to the Impala.

 

He slid into the driver’s seat and just stared ahead for a few minutes. He grinned, the ache in his ass sharper now that he was sitting. Holy fuck, he hoped that lasted a few days.

 

**Notes for the Chapter:**

> So I wanted to work in some canon scenarios of young Dean, and what better way to do that than through Rhonda Hurley? Other authors have written amazing versions of what happened between them and added pegging to the panty-kink. I decided that fit pretty well into what I had here, so there it is. 
> 
> Hope you liked it! I'm a little nervous about this one. It's definitely not my usual content, so let me know what you think!


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